First Time Father and First Time Investor

Cleveland, Ohio
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First Time Father and First Time Investor

Jordan Frisco
Investor · Cleveland · Member since 2022 · 64 posts · 35 votes

At age 29, I am choosing to invest in real estate to better the life I can offer my newborn child. I have spent the last year getting my fixer-upper house ready for our newborn and now (A/C install, patio, fixtures, flooring, plumbing, added bathroom, paint) I will transition into working on readying a rental unit or flipping my first property. I am deciding on finalized strategies:

1. Fix and flip 1-2 properties per year $180-200k purchase (light cosmetic updates), $260k resale, and hang on to 1 rental property a year if I decide I like the rental situation in a middle income area, 1031 exchange

2. Buy and hold Section 8 properties in the Greater Cleveland area, paying $45-55k/door. Acquire 3 properties and sell 1 buy one, 1031 exchange and trade up to a rental property in Parma or Lakewood

3. Fix and flip 1 nice property per year $450-500k resale, 1031 exchange

4. Visit as many nursing homes as I can and convince someone's grandpa to sign their house over to me to fix and flip it and go from there! Haha :)

Where am I going to go wrong? What am I doing right? Open to listen to what you have to say. Thanks!

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James Wise
Real Estate Broker · Cleveland Dayton Cincinnati Toledo Columbus & Akron, OH · Member since 2013 · 30k+ posts · 20k+ votes
1y
Quote from @Jordan Frisco:

At age 29, I am choosing to invest in real estate to better the life I can offer my newborn child. I have spent the last year getting my fixer-upper house ready for our newborn and now (A/C install, patio, fixtures, flooring, plumbing, added bathroom, paint) I will transition into working on readying a rental unit or flipping my first property. I am deciding on finalized strategies:

1. Fix and flip 1-2 properties per year $180-200k purchase (light cosmetic updates), $260k resale, and hang on to 1 rental property a year if I decide I like the rental situation in a middle income area, 1031 exchange

2. Buy and hold Section 8 properties in the Greater Cleveland area, paying $45-55k/door. Acquire 3 properties and sell 1 buy one, 1031 exchange and trade up to a rental property in Parma or Lakewood

3. Fix and flip 1 nice property per year $450-500k resale, 1031 exchange

4. Visit as many nursing homes as I can and convince someone's grandpa to sign their house over to me to fix and flip it and go from there! Haha :)

Where am I going to go wrong? What am I doing right? Open to listen to what you have to say. Thanks!


There isn't gonna be a final strategy that you do your whole career. You do the deals as the opportunities are available. Would you not do a great BRRRR that came across your desk simply because you arbitrarily decided you were going to do a FLIP that year? Doesn't make any sense. Do the deals as the deals become available. Stack the W's.

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  • Kelly BaileyPro Member
    Rental Property Investor · Austin, TX · Member since 2022 · 32 posts · 29 votes
    1y

    I think you may like connecting with Justin & Shelly Nupp. They do fix and flips and if the cashflow will be over $1k per month they typically keep it as a rental.

    2Reply
  • Jordan Frisco
    OP
    Investor · Cleveland · Member since 2022 · 64 posts · 35 votes
    1y

    Thanks Kelly! Hope you're doing well in the Austin heat! 55° last night in Cleveland! 

    0Reply
  • Jamie O'Connell
    Rental Property Investor · Elmira NY · Member since 2023 · 143 posts · 143 votes
    1y

    I personally due the section 8 route. it is not stress free though, section 8 is rough. ! If you can do most of the work yourself, I would try and do a mix of buying, fixing and holding and buying and flipping. Get the monthly cash flow growing while also a mix of the bigger cash outs. 

    2Reply
    • Jordan Frisco
      OP
      Investor · Cleveland · Member since 2022 · 64 posts · 35 votes
      1y
      Quote from @Jamie O'Connell:

      I personally due the section 8 route. it is not stress free though, section 8 is rough. ! If you can do most of the work yourself, I would try and do a mix of buying, fixing and holding and buying and flipping. Get the monthly cash flow growing while also a mix of the bigger cash outs. 

      I think this is one of the better routes for sure. Easy to off load as needed and can remove a lot of headaches after initial inspection and approval from the housing authority. 
      0Reply
    • Jamie O'Connell
      Rental Property Investor · Elmira NY · Member since 2023 · 143 posts · 143 votes
      1y
      Quote from @Jordan Frisco:
      Quote from @Jamie O'Connell:

      I personally due the section 8 route. it is not stress free though, section 8 is rough. ! If you can do most of the work yourself, I would try and do a mix of buying, fixing and holding and buying and flipping. Get the monthly cash flow growing while also a mix of the bigger cash outs. 

      I think this is one of the better routes for sure. Easy to off load as needed and can remove a lot of headaches after initial inspection and approval from the housing authority. 

       Yea definitely. I am not handy myself so I cant (aka dont wanna) do alot of the labor myself. So between that expensive fact and the fact that it's hard to find houses under 200k in my area I dont do it. I firmly believe in my area that after repair value values 300k and under sell MUCH faster than anything above. 

      But if I could find something good I would definitely hop on it because the big cash influx would be nice to help continue buying more income producing properties.

      Real estate is a journey, everyone goes their own route and long as you are looking at all the possible outcomes you will definitely do well. 

      0Reply
    • Jordan Frisco
      OP
      Investor · Cleveland · Member since 2022 · 64 posts · 35 votes
      1y
      Quote from @Jamie O'Connell:
      Quote from @Jordan Frisco:
      Quote from @Jamie O'Connell:

      I personally due the section 8 route. it is not stress free though, section 8 is rough. ! If you can do most of the work yourself, I would try and do a mix of buying, fixing and holding and buying and flipping. Get the monthly cash flow growing while also a mix of the bigger cash outs. 

      I think this is one of the better routes for sure. Easy to off load as needed and can remove a lot of headaches after initial inspection and approval from the housing authority. 

       Yea definitely. I am not handy myself so I cant (aka dont wanna) do alot of the labor myself. So between that expensive fact and the fact that it's hard to find houses under 200k in my area I dont do it. I firmly believe in my area that after repair value values 300k and under sell MUCH faster than anything above. 

      But if I could find something good I would definitely hop on it because the big cash influx would be nice to help continue buying more income producing properties.

      Real estate is a journey, everyone goes their own route and long as you are looking at all the possible outcomes you will definitely do well. 

      I think it is one of the things that people say is passive but they are lying to you because it takes you to be actively engaged mentally to make the right moves, book the right deal, keep a tight schedule and keep the ball moving forward to set yourself up for success. Do you mainly focus on 200-300k houses and do mix off fix and hold and fix and flip?


      0Reply
    • Jamie O'Connell
      Rental Property Investor · Elmira NY · Member since 2023 · 143 posts · 143 votes
      1y
      Quote from @Jordan Frisco:
      Quote from @Jamie O'Connell:
      Quote from @Jordan Frisco:
      Quote from @Jamie O'Connell:

      I personally due the section 8 route. it is not stress free though, section 8 is rough. ! If you can do most of the work yourself, I would try and do a mix of buying, fixing and holding and buying and flipping. Get the monthly cash flow growing while also a mix of the bigger cash outs. 

      I think this is one of the better routes for sure. Easy to off load as needed and can remove a lot of headaches after initial inspection and approval from the housing authority. 

       Yea definitely. I am not handy myself so I cant (aka dont wanna) do alot of the labor myself. So between that expensive fact and the fact that it's hard to find houses under 200k in my area I dont do it. I firmly believe in my area that after repair value values 300k and under sell MUCH faster than anything above. 

      But if I could find something good I would definitely hop on it because the big cash influx would be nice to help continue buying more income producing properties.

      Real estate is a journey, everyone goes their own route and long as you are looking at all the possible outcomes you will definitely do well. 

      I think it is one of the things that people say is passive but they are lying to you because it takes you to be actively engaged mentally to make the right moves, book the right deal, keep a tight schedule and keep the ball moving forward to set yourself up for success. Do you mainly focus on 200-300k houses and do mix off fix and hold and fix and flip?

      No the area I buy is much cheaper (cause it's a crap town) so I do fix and holds. If I could find good fixer uppers where I live in PA though, buying in mid to top 100's and selling for top 200s would prob be my sweet spot. 
      0Reply
  • Candace Hughes
    Real Estate Consultant · Indianapolis IN · Member since 2022 · 22 posts · 20 votes
    1y

    Congrats on taking action and setting clear strategies — that’s already a big win. Your options all have potential, but what stands out is that you’re thinking about both cash flow and long-term growth. Just make sure to keep plenty of reserves, especially if you’re balancing flips with rentals, since timelines and budgets almost always stretch. I’d say your “light cosmetic flip + add a rental each year” path feels like a solid balance between cash and stability. Wishing you success as you get started!

    1Reply
    • Jordan Frisco
      OP
      Investor · Cleveland · Member since 2022 · 64 posts · 35 votes
      1y
      Quote from @Candace Hughes:

      Congrats on taking action and setting clear strategies — that’s already a big win. Your options all have potential, but what stands out is that you’re thinking about both cash flow and long-term growth. Just make sure to keep plenty of reserves, especially if you’re balancing flips with rentals, since timelines and budgets almost always stretch. I’d say your “light cosmetic flip + add a rental each year” path feels like a solid balance between cash and stability. Wishing you success as you get started!

       Thanks Candace. Cash and growth! I would like the cash flow to fuel future growth and move away from troublesome areas that warrant more issues and turnover. I would work to secure higher income rentals that will always be filled and the house appreciates every year. One day I can offload all the properties I don't want and retire with a great chunk of wealth.

      0Reply
    • Candace Hughes
      Real Estate Consultant · Indianapolis IN · Member since 2022 · 22 posts · 20 votes
      1y

      @Jordan Frisco 

      Exactly Jordan, that’s a solid plan. Cash flow fueling growth and trading up into stronger rentals is how you build long-term wealth. You’re definitely on the right track.

      0Reply
    • Jordan Frisco
      OP
      Investor · Cleveland · Member since 2022 · 64 posts · 35 votes
      1y
      Quote from @Candace Hughes:

      Congrats on taking action and setting clear strategies — that’s already a big win. Your options all have potential, but what stands out is that you’re thinking about both cash flow and long-term growth. Just make sure to keep plenty of reserves, especially if you’re balancing flips with rentals, since timelines and budgets almost always stretch. I’d say your “light cosmetic flip + add a rental each year” path feels like a solid balance between cash and stability. Wishing you success as you get started!

      Thanks for the advice! 


      Cash flow and long-term growth are key! I think about the fact that it is just playing real life monopoly. The most important aspect of the game is having the most properties in the end that you can build houses and hotels on, not so much that you have a couple railroads and one utility company. Yeah, you have positive cash flow, but you need a monopoly to win the game!!

      Flips and buy and hold do take cash in reserves, but I think I would have enough to fix a couple thousand dollar fix here and there once I get a year under my belt with just the money that was invested + the amount that is generated in rental income if I play my cards right and get a good tenant in place right away. How much do you set aside as a percentage or dollar amount for your standard investment streategy and why?

      0Reply
  • Brandon Arce
    Member since 2019 · 14 posts · 13 votes
    1y

    Welcome, start with the light renovations, will give you time to get confident to do the bigger renovations and also will allow you to make connections with sub contractors, realtors, etc. I personally would stay away from section 8 and do one small multi-family instead. Let me know how you do with the nursing homes, I might steal that strategy from you, :)

    0Reply
    • Jordan Frisco
      OP
      Investor · Cleveland · Member since 2022 · 64 posts · 35 votes
      1y
      Quote from @Brandon Arce:

      Welcome, start with the light renovations, will give you time to get confident to do the bigger renovations and also will allow you to make connections with sub contractors, realtors, etc. I personally would stay away from section 8 and do one small multi-family instead. Let me know how you do with the nursing homes, I might steal that strategy from you, :)

      Brandon, thanks for the sound advice! Seems different techniques work better for some people. I like what you said about growing in your networking and relationships. At the end of the day who is on your bus with you is more important than the path forward. Reminds me of Jim Collins, "Good to Great" book which states, "First Who, then what!" The best team members that share your vision are what I should focus on more. I think I like Section 8 but I don't know if it works for me or not but I think it is worth a try! MFH are a must if it is not Section 8 in my opinion. 

      0Reply
  • Terrance HillPro Member
    Realtor · Memphis, TN · Member since 2010 · 425 posts · 117 votes
    1y

    Congrats on becoming both a new dad and a new investor, Jordan — that’s awesome motivation! You’ve clearly thought through multiple strategies, which already puts you ahead of the curve. Personally, I think testing out one strategy first (like your cosmetic flips or Section 8 buy-and-holds) will give you clarity before juggling multiple approaches. Either way, you’re setting yourself and your family up for long-term success. Excited to see where you take this journey!

    0Reply
  • James Wise
    Real Estate Broker · Cleveland Dayton Cincinnati Toledo Columbus & Akron, OH · Member since 2013 · 30k+ posts · 20k+ votes
    1y
    Quote from @Jordan Frisco:

    At age 29, I am choosing to invest in real estate to better the life I can offer my newborn child. I have spent the last year getting my fixer-upper house ready for our newborn and now (A/C install, patio, fixtures, flooring, plumbing, added bathroom, paint) I will transition into working on readying a rental unit or flipping my first property. I am deciding on finalized strategies:

    1. Fix and flip 1-2 properties per year $180-200k purchase (light cosmetic updates), $260k resale, and hang on to 1 rental property a year if I decide I like the rental situation in a middle income area, 1031 exchange

    2. Buy and hold Section 8 properties in the Greater Cleveland area, paying $45-55k/door. Acquire 3 properties and sell 1 buy one, 1031 exchange and trade up to a rental property in Parma or Lakewood

    3. Fix and flip 1 nice property per year $450-500k resale, 1031 exchange

    4. Visit as many nursing homes as I can and convince someone's grandpa to sign their house over to me to fix and flip it and go from there! Haha :)

    Where am I going to go wrong? What am I doing right? Open to listen to what you have to say. Thanks!


    There isn't gonna be a final strategy that you do your whole career. You do the deals as the opportunities are available. Would you not do a great BRRRR that came across your desk simply because you arbitrarily decided you were going to do a FLIP that year? Doesn't make any sense. Do the deals as the deals become available. Stack the W's.

    3Reply
    • Jordan Frisco
      OP
      Investor · Cleveland · Member since 2022 · 64 posts · 35 votes
      1y
      Quote from @James Wise:
      Quote from @Jordan Frisco:

      At age 29, I am choosing to invest in real estate to better the life I can offer my newborn child. I have spent the last year getting my fixer-upper house ready for our newborn and now (A/C install, patio, fixtures, flooring, plumbing, added bathroom, paint) I will transition into working on readying a rental unit or flipping my first property. I am deciding on finalized strategies:

      1. Fix and flip 1-2 properties per year $180-200k purchase (light cosmetic updates), $260k resale, and hang on to 1 rental property a year if I decide I like the rental situation in a middle income area, 1031 exchange

      2. Buy and hold Section 8 properties in the Greater Cleveland area, paying $45-55k/door. Acquire 3 properties and sell 1 buy one, 1031 exchange and trade up to a rental property in Parma or Lakewood

      3. Fix and flip 1 nice property per year $450-500k resale, 1031 exchange

      4. Visit as many nursing homes as I can and convince someone's grandpa to sign their house over to me to fix and flip it and go from there! Haha :)

      Where am I going to go wrong? What am I doing right? Open to listen to what you have to say. Thanks!


      There isn't gonna be a final strategy that you do your whole career. You do the deals as the opportunities are available. Would you not do a great BRRRR that came across your desk simply because you arbitrarily decided you were going to do a FLIP that year? Doesn't make any sense. Do the deals as the deals become available. Stack the W's.

      Awesome that you replied James Wise! Drive by your shop on Brookpark all the time. Watched a good bit of your videos over the years. You have a fire in your belly for real estate and all things Cleveland. My favorite videos were the tenants from hell. I have some similar experiences I can relate doing renovation work around E 55th and superior over the years.

      This is so true. I value options and being flexible to modify my strategy at every opportunity that presents itself. At the same time I know real estate is something I need to get serious about and not waiting on things to happen or over analyzing deals. What do you think the most important aspect of knowing yourself is for first starting off? Is it your allocated time, the money willing to invest, the location, the level of involvement (at home or at site), your partners, or a combination of all of it? 
      0Reply
    • James Wise
      Real Estate Broker · Cleveland Dayton Cincinnati Toledo Columbus & Akron, OH · Member since 2013 · 30k+ posts · 20k+ votes
      1y
      Quote from @Jordan Frisco:
      Quote from @James Wise:
      Quote from @Jordan Frisco:

      At age 29, I am choosing to invest in real estate to better the life I can offer my newborn child. I have spent the last year getting my fixer-upper house ready for our newborn and now (A/C install, patio, fixtures, flooring, plumbing, added bathroom, paint) I will transition into working on readying a rental unit or flipping my first property. I am deciding on finalized strategies:

      1. Fix and flip 1-2 properties per year $180-200k purchase (light cosmetic updates), $260k resale, and hang on to 1 rental property a year if I decide I like the rental situation in a middle income area, 1031 exchange

      2. Buy and hold Section 8 properties in the Greater Cleveland area, paying $45-55k/door. Acquire 3 properties and sell 1 buy one, 1031 exchange and trade up to a rental property in Parma or Lakewood

      3. Fix and flip 1 nice property per year $450-500k resale, 1031 exchange

      4. Visit as many nursing homes as I can and convince someone's grandpa to sign their house over to me to fix and flip it and go from there! Haha :)

      Where am I going to go wrong? What am I doing right? Open to listen to what you have to say. Thanks!


      There isn't gonna be a final strategy that you do your whole career. You do the deals as the opportunities are available. Would you not do a great BRRRR that came across your desk simply because you arbitrarily decided you were going to do a FLIP that year? Doesn't make any sense. Do the deals as the deals become available. Stack the W's.

      Awesome that you replied James Wise! Drive by your shop on Brookpark all the time. Watched a good bit of your videos over the years. You have a fire in your belly for real estate and all things Cleveland. My favorite videos were the tenants from hell. I have some similar experiences I can relate doing renovation work around E 55th and superior over the years.

      This is so true. I value options and being flexible to modify my strategy at every opportunity that presents itself. At the same time I know real estate is something I need to get serious about and not waiting on things to happen or over analyzing deals. What do you think the most important aspect of knowing yourself is for first starting off? Is it your allocated time, the money willing to invest, the location, the level of involvement (at home or at site), your partners, or a combination of all of it? 

       Money

      0Reply
  • Min ZhangBusiness Member
    Real Estate Agent · Member since 2022 · 1k+ posts · 1k+ votes
    1y

    Jordan, love how you laid out multiple paths! you’re clearly thinking this through. A couple thoughts:

    Fix/flip is great for building chunks of cash, but it can eat up more time and energy than expected, especially when holding costs stretch out or buyers retrade after inspection. On the other hand, Section 8 rentals in working-class areas can be a steady play if you’re comfortable with city inspections and the paperwork. I’ve seen folks do well mixing both, flip a house or two a year to generate capital, then park those profits into buy-and-holds that cash flow and appreciate.

     Focus on one lane, build systems, and then layer in the next. Out of your options, which excites you more right now? the active side (flipping) or the long-term passive income side (rentals)?

    [email protected]614-412-2912
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    • Jordan Frisco
      OP
      Investor · Cleveland · Member since 2022 · 64 posts · 35 votes
      1y
      Quote from @Min Zhang:

      Jordan, love how you laid out multiple paths! you’re clearly thinking this through. A couple thoughts:

      Fix/flip is great for building chunks of cash, but it can eat up more time and energy than expected, especially when holding costs stretch out or buyers retrade after inspection. On the other hand, Section 8 rentals in working-class areas can be a steady play if you’re comfortable with city inspections and the paperwork. I’ve seen folks do well mixing both, flip a house or two a year to generate capital, then park those profits into buy-and-holds that cash flow and appreciate.

       Focus on one lane, build systems, and then layer in the next. Out of your options, which excites you more right now? the active side (flipping) or the long-term passive income side (rentals)?

      Love the idea - one lane, one path, one vision forward! Energy is the ultimate resource for sure! I would say Section 8 is pretty exciting and so is MFH buy and hold.
      1Reply
  • Arman AhmedPro Member
    Real Estate Agent · Columbus Cleveland Dayton, OH · Member since 2024 · 2k+ posts · 924 votes
    1y

    @Jordan Frisco

    Jordan, congrats on becoming a new dad—that’s amazing motivation to invest! From what you laid out, you’re already thinking like an investor with clear strategies. The biggest thing I’d watch out for is overestimating resale values on flips and underestimating repair/holding costs, especially in today’s market where margins can get tight. On the Section 8 side in Cleveland, you’re on the right track—those $45–55k doors can cash flow well if you buy in the right areas and have reliable management. My advice would be to pick one strategy to focus on first (flip or buy-and-hold) rather than splitting attention. That way you build momentum and systems before scaling into multiple approaches.

    [email protected]614-418-6081
    1Reply
    • Jordan Frisco
      OP
      Investor · Cleveland · Member since 2022 · 64 posts · 35 votes
      1y
      Quote from @Arman Ahmed:

      @Jordan Frisco

      Jordan, congrats on becoming a new dad—that’s amazing motivation to invest! From what you laid out, you’re already thinking like an investor with clear strategies. The biggest thing I’d watch out for is overestimating resale values on flips and underestimating repair/holding costs, especially in today’s market where margins can get tight. On the Section 8 side in Cleveland, you’re on the right track—those $45–55k doors can cash flow well if you buy in the right areas and have reliable management. My advice would be to pick one strategy to focus on first (flip or buy-and-hold) rather than splitting attention. That way you build momentum and systems before scaling into multiple approaches.

      Your post looks like it was generated with AI. 
      0Reply
  • Dave FosterBusiness Member
    Qualified Intermediary for 1031 Exchanges · St. Petersburg, FL · Member since 2013 · 9k+ posts · 9k+ votes
    1y


    @Jordan Frisco, these could all be great strategies, but ultimately, a lot will be determined by how much time you can invest in your properties, what your local market conditions look like, and lastly, what aligns with your future goals.

    1031 exchanges are primarily for investment properties that are held for investment use. Fix n flips don't meet this criteria because they are not purchased with the intent to hold for productive use; they are more so looked at as inventory. Occasionally, an investor will purchase an investment property with the intent to hold, and a negative catalyst will cause them to prematurely sell despite that intent, but I wouldn't bet on those happening on a regular basis. But there are ways to get the quicker cash from a fix and flip model while still using 1031s to defer the high tax of a fix and flip model. You just have to tweak your model a little.

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    • Jordan Frisco
      OP
      Investor · Cleveland · Member since 2022 · 64 posts · 35 votes
      1y
      Quote from @Dave Foster:


      @Jordan Frisco, these could all be great strategies, but ultimately, a lot will be determined by how much time you can invest in your properties, what your local market conditions look like, and lastly, what aligns with your future goals.

      1031 exchanges are primarily for investment properties that are held for investment use. Fix n flips don't meet this criteria because they are not purchased with the intent to hold for productive use; they are more so looked at as inventory. Occasionally, an investor will purchase an investment property with the intent to hold, and a negative catalyst will cause them to prematurely sell despite that intent, but I wouldn't bet on those happening on a regular basis. But there are ways to get the quicker cash from a fix and flip model while still using 1031s to defer the high tax of a fix and flip model. You just have to tweak your model a little.

      Dave, "...prematurely sell despite that intent,..." is definitely a reality I need to prepare for and an exit plan written in the initial plan I make should be considered along with my criteria for my risk tolerance. I appreciate this input. 

      Am I understanding your summary? The success of any real estate strategy hinges on:

      • How much time I can dedicate to managing properties.
      • Please clarify -> Do not bet on 1031 exchanges on a regular basis or the negative intent?
      • Your long-term financial and lifestyle goals
      I think I need to unpack this strategy more in the future when I know more about real estate -> "But there are ways to get the quicker cash from a fix and flip model while still using 1031s to defer the high tax of a fix and flip model" It seems like a lot of big guys out there use 1031 ad-nauseam and extensively across all investment forms. Is this based off the capital gains tax (leverage 1+ year flips to avoid capital gains tax) or just roll it into inventory like you were saying before and it is treated like a business?


      0Reply
  • Kerlous TadresBusiness Member
    Realtor · Columbus, OH · Member since 2023 · 1k+ posts · 1k+ votes
    1y

    Hey @Jordan Frisco! From my experience, you’re already thinking like an investor, setting clear targets and running the numbers. Light fix-and-flips with a rental hold is a solid way to build both cash and long-term equity. Just be sure you’re buying with enough spread and budgeting for higher interest rates, holding costs, and a 10–15% buffer for surprises. Section 8 buy-and-hold in Cleveland can work well if you stay strict on location and have a property manager who knows the voucher system inside and out; I’d focus on B- to C+ neighborhoods with stable tenant bases. Higher-end flips can bring big profits, but higher price points move slower and carry more risk if the market cools, so only consider those when you have strong comps and a deep cash cushion. The “grandpa’s house” hustle is funny but really just networking for off-market deals, driving for dollars, probate lists can achieve the same thing without relying on chance. If it were me, I’d start with the smaller flips and hold a good rental each year for steady learning, manageable risk, and the flexibility to pivot as you grow.

    @Jordan Friscoundefined

    [email protected]614-490-1163
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    1Reply
    • Jordan Frisco
      OP
      Investor · Cleveland · Member since 2022 · 64 posts · 35 votes
      1y
      Quote from @Kerlous Tadres:

      Hey @Jordan Frisco! From my experience, you’re already thinking like an investor, setting clear targets and running the numbers. Light fix-and-flips with a rental hold is a solid way to build both cash and long-term equity. Just be sure you’re buying with enough spread and budgeting for higher interest rates, holding costs, and a 10–15% buffer for surprises. Section 8 buy-and-hold in Cleveland can work well if you stay strict on location and have a property manager who knows the voucher system inside and out; I’d focus on B- to C+ neighborhoods with stable tenant bases. Higher-end flips can bring big profits, but higher price points move slower and carry more risk if the market cools, so only consider those when you have strong comps and a deep cash cushion. The “grandpa’s house” hustle is funny but really just networking for off-market deals, driving for dollars, probate lists can achieve the same thing without relying on chance. If it were me, I’d start with the smaller flips and hold a good rental each year for steady learning, manageable risk, and the flexibility to pivot as you grow.

      @Jordan Friscoundefined

      Love these recommendations and pieced of advice- 
      discipline is everything, higher end flips carry risk, light fix and flips

      Can you unpack what you mean when you say "...higher price points move slower and carry more risk if the market cools..." I think this would only be true in the $425k+ houses in Cleveland and $450+ houses in Cbus. I think higher end flips are much better to do down the line when I have a contractor base that I can feed enough work to in the mid to lower range flips and can afford to float a lot more cash as I grow. I like MFHs and section 8 right now. I like what you recommend on the smaller flips and good buy and hold rentals. I think it is just a matter of getting in the game and getting my teeth kicked in a few times and learn the ropes. 

      I need to focus on execution rather than festering about path forward. The snowball needs to get smashed into formation before it starts to grow...

      0Reply
  • Matthew Paul
    Severna Park, MD · Member since 2013 · 7k+ posts · 7k+ votes
    1y

    @Jordan Frisco  Nice plan , maybe 

    You said you are a first time investor . where are your funds coming from ?  Any construction experience ?  Any property management experience ?  Whats going to happen on section 8 properties when the administration cuts funds and limits people to 2 years ?  Do you know any contractors ? 

    Just remember this when you are investing you can also lose money if things dont go as planned .        

    0Reply
  • Drew SygitBusiness Member
    Property Manager · Royal Oak, MI · Member since 2012 · 12k+ posts · 9k+ votes
    1y

    @Jordan Frisco I spent 4 years working a day job and spending nights & weekends working on flips & rentals - before I got burned out!

    Focus on finding better & better deals as you build your network.

    The property, deal, your time, and your finances @ that moment, will determine what you should do with each deal you find. 

    You forgot to add "wholesaling" or referrring a deal to another investor for a fee - without doing anything. You'll do that on deals you don't have the time or money for or that don't meet your BuyBox.

    Neer forget, your Network => Your Net Worth!

    [email protected]248-209-6824
    Logical Property Management4.9458 Reviews
    WebsiteView Page
    1Reply
    • Jordan Frisco
      OP
      Investor · Cleveland · Member since 2022 · 64 posts · 35 votes
      1y
      Quote from @Drew Sygit:

      @Jordan Frisco I spent 4 years working a day job and spending nights & weekends working on flips & rentals - before I got burned out!

      Focus on finding better & better deals as you build your network.

      The property, deal, your time, and your finances @ that moment, will determine what you should do with each deal you find. 

      You forgot to add "wholesaling" or referrring a deal to another investor for a fee - without doing anything. You'll do that on deals you don't have the time or money for or that don't meet your BuyBox.

      Neer forget, your Network => Your Net Worth!

      Wholesaling would probably be the least desirable for me - maybe it is different for others. I just feel you cannot leverage debt against the money you put into the property with that strategy. That being said, everybody and every strategy has a price and it may be worth it if the right deal come across my desk!

      Your quote, "The property, deal, your time, and your finances @ that moment, will determine what you should do with each deal you find." hits home to me. The biggest thing I felt reading this is the importance of time and your finances at that moment! I feel I have spent years working on W2 income, investing in the stock market and diversifying, and getting on the right track and staying there financially that I am ready to leverage some money against the future appreciation, value, and cash flow that I am more risk tolerant to put up money in homes that bring a strong future value and promising cash flow. 


      0Reply
    • Drew SygitBusiness Member
      Property Manager · Royal Oak, MI · Member since 2012 · 12k+ posts · 9k+ votes
      1y
      Quote from @Jordan Frisco:
      Quote from @Drew Sygit:

      @Jordan Frisco I spent 4 years working a day job and spending nights & weekends working on flips & rentals - before I got burned out!

      Focus on finding better & better deals as you build your network.

      The property, deal, your time, and your finances @ that moment, will determine what you should do with each deal you find. 

      You forgot to add "wholesaling" or referrring a deal to another investor for a fee - without doing anything. You'll do that on deals you don't have the time or money for or that don't meet your BuyBox.

      Neer forget, your Network => Your Net Worth!

      Wholesaling would probably be the least desirable for me - maybe it is different for others. I just feel you cannot leverage debt against the money you put into the property with that strategy. That being said, everybody and every strategy has a price and it may be worth it if the right deal come across my desk!

      Your quote, "The property, deal, your time, and your finances @ that moment, will determine what you should do with each deal you find." hits home to me. The biggest thing I felt reading this is the importance of time and your finances at that moment! I feel I have spent years working on W2 income, investing in the stock market and diversifying, and getting on the right track and staying there financially that I am ready to leverage some money against the future appreciation, value, and cash flow that I am more risk tolerant to put up money in homes that bring a strong future value and promising cash flow. 



       With wholesaling, YOU do not buy the property. You "sell" the contract to another investor. 
      NOTE: you have to be careful to do this legally or at least know the consequences...

      [email protected]248-209-6824
      Logical Property Management4.9458 Reviews
      WebsiteView Page
      0Reply
  • Gladimir Lobo
    Real Estate Broker · Cleveland, OH · Member since 2023 · 214 posts · 81 votes
    1y

    Congrats on your bundle of joy. You should check out GLREIA Focus Group. Last meetings were 🔥 we swapped stories on hiring and screening contractors (the good, the bad, and the sketchy 😅).

    If you're a landlord or investor in Cleveland, this is the crew you want to roll with. Real talk, real tips, and people who actually get it. Hit me up if you want to be my guest.

    0Reply
    • Jordan Frisco
      OP
      Investor · Cleveland · Member since 2022 · 64 posts · 35 votes
      1y
      Quote from @Gladimir Lobo:

      Congrats on your bundle of joy. You should check out GLREIA Focus Group. Last meetings were 🔥 we swapped stories on hiring and screening contractors (the good, the bad, and the sketchy 😅).

      If you're a landlord or investor in Cleveland, this is the crew you want to roll with. Real talk, real tips, and people who actually get it. Hit me up if you want to be my guest.

      Gladimir, I will reply to any and all inquiries in the Bigger Pockets community. Feel free to reach out. Let's talk Cleveland, Guardians, Browns, Cavs you name it!

      0Reply
  • Joseph TadresPro Member
    Real Estate Agent · Columbus, OH · Member since 2025 · 184 posts · 179 votes
    1y

    You’re on the right track. From my experience, start with the mid-range flips, $180–200k buys with light updates sell fast and let you build a solid contractor team. Hold one as a rental if it cash flows.

    Cleveland Section 8 can work for steady income, just budget for inspections and strong property management. I’d wait on the $450k flips until you’ve got a few smaller wins under your belt.

    0Reply
    • Jordan Frisco
      OP
      Investor · Cleveland · Member since 2022 · 64 posts · 35 votes
      1y
      Quote from @Joseph Tadres:

      You’re on the right track. From my experience, start with the mid-range flips, $180–200k buys with light updates sell fast and let you build a solid contractor team. Hold one as a rental if it cash flows.

      Cleveland Section 8 can work for steady income, just budget for inspections and strong property management. I’d wait on the $450k flips until you’ve got a few smaller wins under your belt.

      Joseph, I like this strategy! I think opening myself up to this and also hold a little bit longer and refinance is definitely the right place to start and consider. It can change with the project scope of the fix but I think being flexible after month 2-3 can produce a good path forward!

      1Reply
  • Dave FosterBusiness Member
    Qualified Intermediary for 1031 Exchanges · St. Petersburg, FL · Member since 2013 · 9k+ posts · 9k+ votes
    1y

    @Jordan Frisco, Thanks for the kind words. There's different successful models everwhere. Because success doesn't just depend on the tools you use (like the 1031). It depends on your unique situation as well. The most common model I've seen that allows fix and flippers to also do 1031s the the tried and true BRRRR method. Instead of fixing and flipping you fix hold refi and use the tax freee refi cash to add more properties or live on. And then when you sell a property it is now eligible a 1031 exchange which indefinitely defers all of the tax on gain. I've had clients doing 20-30 exchanges a year. All on properties they bought to fix and value add. But also all on properties they had owned more than a year so they could take advantage of cash out refis and 1031 exchanges.

    The 1031 Investor5137 Reviews
    WebsiteView Page
    1Reply
    • Jordan Frisco
      OP
      Investor · Cleveland · Member since 2022 · 64 posts · 35 votes
      1y
      Quote from @Dave Foster:

      @Jordan Frisco, Thanks for the kind words. There's different successful models everwhere. Because success doesn't just depend on the tools you use (like the 1031). It depends on your unique situation as well. The most common model I've seen that allows fix and flippers to also do 1031s the the tried and true BRRRR method. Instead of fixing and flipping you fix hold refi and use the tax freee refi cash to add more properties or live on. And then when you sell a property it is now eligible a 1031 exchange which indefinitely defers all of the tax on gain. I've had clients doing 20-30 exchanges a year. All on properties they bought to fix and value add. But also all on properties they had owned more than a year so they could take advantage of cash out refis and 1031 exchanges.

      I agree. The BRRRR method is not as worth it unless you can maximize on the last two R's! Without the leverage of the property with debt you can only go so far. I will look more into those windows of opportunity of refinance and repeat as I move forward.

      0Reply
  • Josh L.
    USA · Member since 2023 · 145 posts · 84 votes
    1y

    @Jordan Frisco - Nice post. I think option 1 is a good idea if you don't have a W2 (even better if you do) to help with capital as you would use your flips (active income) to help fund your holds. Just my thoughts based on what you've outlined. 

    0Reply
    • Jordan Frisco
      OP
      Investor · Cleveland · Member since 2022 · 64 posts · 35 votes
      1y
      Quote from @Josh L.:

      @Jordan Frisco - Nice post. I think option 1 is a good idea if you don't have a W2 (even better if you do) to help with capital as you would use your flips (active income) to help fund your holds. Just my thoughts based on what you've outlined. 

      Thanks Josh! I feel it may be the one I go with depending on my finite resource of time and the infinite ways to make money in real estate. I feel it leaves my options open for exploration into different strategies if I plan to be prepared for both parts of Option #1

      1Reply
  • Drago Stanimirovic
    New to Real Estate · Miami, FL · Member since 2024 · 1k+ posts · 455 votes
    1y

    Jordan, you’re thinking like a true investor already, great mix of strategy and hustle.

    What you’re doing right: building equity, planning exits, and staying flexible. Where it can go wrong is trying too many approaches too soon. Start with one (like $180-200k flips or mid-tier rentals), build experience and cash flow, then scale.

    And option 4, funny, but with the right probate strategy, not far off!

    You’ve got a solid foundation. Keep going.

    0Reply
    • Jordan Frisco
      OP
      Investor · Cleveland · Member since 2022 · 64 posts · 35 votes
      1y
      Quote from @Drago Stanimirovic:

      Jordan, you’re thinking like a true investor already, great mix of strategy and hustle.

      What you’re doing right: building equity, planning exits, and staying flexible. Where it can go wrong is trying too many approaches too soon. Start with one (like $180-200k flips or mid-tier rentals), build experience and cash flow, then scale.

      And option 4, funny, but with the right probate strategy, not far off!

      You’ve got a solid foundation. Keep going.

      Love this comment. Equity, planning exits, and staying flexible. Those are key to finding success in my opinion. I have sometimes jumped in without that exit strategy in other aspects of my life and paid the price on it! I love the idea of being flexible enough to move and pivot on a deal but also cutting bait when it is time to say goodbye!


      1Reply
  • Zachariah HaysPro Member
    Realtor · Cleveland, OH · Member since 2025 · 18 posts · 4 votes
    1y

    Congrats on the family Jordan. Like you, I am working on setting up my family foundation early on (32) for cash flow and appreciation as well. 

    I am a local Cleveland investor myself who does cosmetic flips and adds rentals each year. 

    You are thinking in the right direction as far as your goals go. In my biased opinion, I'd start with light cosmetic flips/renrals (as I did) to gain connections with contractors, get experience and add lenders. 

    Doing lighter lifts in the beginning will build confidence with repetition and you can take on a little more with each project. Glad to talk through things more here online or locally. 

    [email protected]
    0Reply
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