Super Rookie Here. Looking for direction PLEASE!

Super Rookie Here. Looking for direction PLEASE!

Member since 2022 · 10 posts · 7 votes

Hello everyone,

My name is Steve and at 46 years old, I'm looking to possibly start a STR business and while I've been doing a lot of research, I guess I'm feeling a little lost (or maybe overwhelmed is a better way of describing it).

For a little background, I'm currently a W2 employee (and have been always). My wife is as well. We moved to Florida 2 years ago and love it here. We're currently outside of Orlando and have been looking to find something in our backyard (within 30ish miles or so)

Our situation:

    -We have pretty much no debt at all, including owning our home. We do owe a bit on a Truck we bought earlier in the year, but that's it. No CC debt or any other consumer debt.

    -Our current home is probably worth around $500 - $550 (with current market conditions)

    -We wanted to focus on having no debt, but now we also aren't left with a lot of capital and very little in retirement (hence our desire to look into real estate to help build wealth and recurring income). Would be nice to retire someday haha.

So, I guess I'm just wondering how to get started since we don't have a ton for a down payment (could probably come up with $25k in cash without touching a current 401k that's not all that large).

Also, the Orlando area (and outlying area) looks to be pretty saturated, but there is also a TON of tourist's that visit here too so I'm not sure if one cancels out the other in this type of business. I would be willing to look at other markets here in Florida such as Tampa, Sarasota, Pensacola or other similar type of places, I just haven't done much research into those areas yet. And, since we're just starting out and wanting to learn the business, we thought it best to stay as close to home as we could for the time being.

Anyway, consider me a dry sponge. I'm willing to learn as much as I can as we look to start into this business. I'd love any advice, tips, thoughts, concerns, or anything else you have to offer a rookie like me.

Thank you all so much and I sincerely appreciate you taking any time you can spare to help us out!

Steve



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Don KonipolBusiness Member
Investor · The Woodlands TX / Avon, CT · Member since 2009 · 6k+ posts · 10k+ votes
4y
Quote from @Steve Uekert:

Hello everyone,

My name is Steve and at 46 years old, I'm looking to possibly start a STR business and while I've been doing a lot of research, I guess I'm feeling a little lost (or maybe overwhelmed is a better way of describing it).

For a little background, I'm currently a W2 employee (and have been always). My wife is as well. We moved to Florida 2 years ago and love it here. We're currently outside of Orlando and have been looking to find something in our backyard (within 30ish miles or so)

Our situation:

    -We have pretty much no debt at all, including owning our home. We do owe a bit on a Truck we bought earlier in the year, but that's it. No CC debt or any other consumer debt.

    -Our current home is probably worth around $500 - $550 (with current market conditions)

    -We wanted to focus on having no debt, but now we also aren't left with a lot of capital and very little in retirement (hence our desire to look into real estate to help build wealth and recurring income). Would be nice to retire someday haha.

So, I guess I'm just wondering how to get started since we don't have a ton for a down payment (could probably come up with $25k in cash without touching a current 401k that's not all that large).

Also, the Orlando area (and outlying area) looks to be pretty saturated, but there is also a TON of tourist's that visit here too so I'm not sure if one cancels out the other in this type of business. I would be willing to look at other markets here in Florida such as Tampa, Sarasota, Pensacola or other similar type of places, I just haven't done much research into those areas yet. And, since we're just starting out and wanting to learn the business, we thought it best to stay as close to home as we could for the time being.

Anyway, consider me a dry sponge. I'm willing to learn as much as I can as we look to start into this business. I'd love any advice, tips, thoughts, concerns, or anything else you have to offer a rookie like me.

Thank you all so much and I sincerely appreciate you taking any time you can spare to help us out!

Steve



Okay Steve, here’s the BIGGEST obstacle you have to overcome: you’re uncomfortable with debt.  In my 40 plus years in the real estate industry, I know of no one who started out with limited capital who made significant money without incurring debt, and usually a lot of it!.

So, you have a pretty common misunderstanding; you don’t distinguish between “good” debt and “bad” debt.  Bad debt isn”t actually bad, rather it’s unproductive, and can be bad if overused, or abused.  This is debt taken on to purchase DEPRECIATING, non income producing assets, like cars for personal use, vacations, food, clothing, etc.  Most credit card debt, auto loans, personal loans used for consumer purchases fall under this category.

The “good” debt isn’t actually good, rather its productive.  This is debt that help you acquire assets that either APPRECIATE in value, throw off income, or better yet do both.  So for example a commercial building with a class A tenant paying a NNN rent of $120,000 a year acquired for $800,000.  But you only can come up with $200,000.  You borrow the other $600,000 secured by the property.  In 5 years you’ve collected $400,000 cash flow over your note payments; paid down you’re loan from $600,000 to $550,000, and the value of the property increased from $800,000 to $1 million.  Now these deals are rare, and may not exist in this low interest rate environment, but they do happen.  And you can see that taking on the debt was a good idea.  

In any case, once most investors reach a certain level of wealth, which differs for each person, they either eliminate debt all together, or, better still, they only incur debt for which they have no personal liability.  

However, if someone is so uncomfortable with debt that they can’t emotionally separate debt for investment from debt for consumer items, than they’re probably better off limiting their expectations at to the beneficial aspects of real property investing.  There will still be some benefits such as cash flow and inflation hedge, but the major benefit, leverage, will be eliminated and it will take 30 years to accomplish what can be done in 10 utilizing moderate debt with a moderate degree of risk.


Private Mortgage Financing Partners, LLC
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14 Replies

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  • Luke CarlPro Member
    Rental Property Investor · Tennessee Florida · Member since 2016 · 4k+ posts · 5k+ votes
    4y

    Read Avery’s book! Short term rental long term wealth 

  • Real Estate Agent · Smoky Mountains, TN · Member since 2022 · 1k+ posts · 984 votes
    4y

    You can do it. Literally almost anywhere as long as the numbers work. Happy to discuss!

  • Bruce WoodruffPro Member
    Contractor/Investor/Consultant · San Diego / Phoenix · Member since 2021 · 12k+ posts · 15k+ votes
    4y

    Get a HELOC on your paid-off house and buy a rental. Then Refi that and repeat...

    I know that sounds incredibly simple, but there ain't a whole lot more to it.....

  • Don KonipolBusiness Member
    Investor · The Woodlands TX / Avon, CT · Member since 2009 · 6k+ posts · 10k+ votes
    4y
    Quote from @Steve Uekert:

    Hello everyone,

    My name is Steve and at 46 years old, I'm looking to possibly start a STR business and while I've been doing a lot of research, I guess I'm feeling a little lost (or maybe overwhelmed is a better way of describing it).

    For a little background, I'm currently a W2 employee (and have been always). My wife is as well. We moved to Florida 2 years ago and love it here. We're currently outside of Orlando and have been looking to find something in our backyard (within 30ish miles or so)

    Our situation:

        -We have pretty much no debt at all, including owning our home. We do owe a bit on a Truck we bought earlier in the year, but that's it. No CC debt or any other consumer debt.

        -Our current home is probably worth around $500 - $550 (with current market conditions)

        -We wanted to focus on having no debt, but now we also aren't left with a lot of capital and very little in retirement (hence our desire to look into real estate to help build wealth and recurring income). Would be nice to retire someday haha.

    So, I guess I'm just wondering how to get started since we don't have a ton for a down payment (could probably come up with $25k in cash without touching a current 401k that's not all that large).

    Also, the Orlando area (and outlying area) looks to be pretty saturated, but there is also a TON of tourist's that visit here too so I'm not sure if one cancels out the other in this type of business. I would be willing to look at other markets here in Florida such as Tampa, Sarasota, Pensacola or other similar type of places, I just haven't done much research into those areas yet. And, since we're just starting out and wanting to learn the business, we thought it best to stay as close to home as we could for the time being.

    Anyway, consider me a dry sponge. I'm willing to learn as much as I can as we look to start into this business. I'd love any advice, tips, thoughts, concerns, or anything else you have to offer a rookie like me.

    Thank you all so much and I sincerely appreciate you taking any time you can spare to help us out!

    Steve



    Okay Steve, here’s the BIGGEST obstacle you have to overcome: you’re uncomfortable with debt.  In my 40 plus years in the real estate industry, I know of no one who started out with limited capital who made significant money without incurring debt, and usually a lot of it!.

    So, you have a pretty common misunderstanding; you don’t distinguish between “good” debt and “bad” debt.  Bad debt isn”t actually bad, rather it’s unproductive, and can be bad if overused, or abused.  This is debt taken on to purchase DEPRECIATING, non income producing assets, like cars for personal use, vacations, food, clothing, etc.  Most credit card debt, auto loans, personal loans used for consumer purchases fall under this category.

    The “good” debt isn’t actually good, rather its productive.  This is debt that help you acquire assets that either APPRECIATE in value, throw off income, or better yet do both.  So for example a commercial building with a class A tenant paying a NNN rent of $120,000 a year acquired for $800,000.  But you only can come up with $200,000.  You borrow the other $600,000 secured by the property.  In 5 years you’ve collected $400,000 cash flow over your note payments; paid down you’re loan from $600,000 to $550,000, and the value of the property increased from $800,000 to $1 million.  Now these deals are rare, and may not exist in this low interest rate environment, but they do happen.  And you can see that taking on the debt was a good idea.  

    In any case, once most investors reach a certain level of wealth, which differs for each person, they either eliminate debt all together, or, better still, they only incur debt for which they have no personal liability.  

    However, if someone is so uncomfortable with debt that they can’t emotionally separate debt for investment from debt for consumer items, than they’re probably better off limiting their expectations at to the beneficial aspects of real property investing.  There will still be some benefits such as cash flow and inflation hedge, but the major benefit, leverage, will be eliminated and it will take 30 years to accomplish what can be done in 10 utilizing moderate debt with a moderate degree of risk.


    Private Mortgage Financing Partners, LLC
  • Member since 2022 · 10 posts · 7 votes
    4y
    Quote from @Don Konipol:

    So, you have a pretty common misunderstanding; you don’t distinguish between “good” debt and “bad” debt.  Bad debt isn”t actually bad, rather it’s unproductive, and can be bad if overused, or abused.  This is debt taken on to purchase DEPRECIATING, non income producing assets, like cars for personal use, vacations, food, clothing, etc.  Most credit card debt, auto loans, personal loans used for consumer purchases fall under this category.

    The “good” debt isn’t actually good, rather its productive.  This is debt that help you acquire assets that either APPRECIATE in value, throw off income, or better yet do both.  So for example a commercial building with a class A tenant paying a NNN rent of $120,000 a year acquired for $800,000.  But you only can come up with $200,000.  You borrow the other $600,000 secured by the property.  In 5 years you’ve collected $400,000 cash flow over your note payments; paid down you’re loan from $600,000 to $550,000, and the value of the property increased from $800,000 to $1 million.  Now these deals are rare, and may not exist in this low interest rate environment, but they do happen.  And you can see that taking on the debt was a good idea.  

    In any case, once most investors reach a certain level of wealth, which differs for each person, they either eliminate debt all together, or, better still, they only incur debt for which they have no personal liability.  

    However, if someone is so uncomfortable with debt that they can’t emotionally separate debt for investment from debt for consumer items, than they’re probably better off limiting their expectations at to the beneficial aspects of real property investing.  There will still be some benefits such as cash flow and inflation hedge, but the major benefit, leverage, will be eliminated and it will take 30 years to accomplish what can be done in 10 utilizing moderate debt with a moderate degree of risk.



     Hi Don!

    I'm planning on responding to everyone, but wanted to take a moment to respond to this post as I think you got to the heart of some of the feelings I've had since I began thinking and researching this business.

    Yes, I've been uncomfortable with debt for most of my life due to seeing debt ruin people around me. However, I'd like to think that while I'm uncomfortable with debt, that I'm not afraid of it as long as it most definitely qualifies as the "good" or "productive" debt. In fact, my wife and I have had a lot of discussion about this and one of the first things we talked about what about risk and how we're going to have to get comfortable with it.

    We're not risk averse, but we've definitely gotten comfortable and are willing to step out in faith. Having no debt is great, as long as you have the income or wealth to be able to retire without having to sell everything to live. And right now, I feel that's where we'd be at. So I'm more willing than ever to embrace the right kind of debt.

    Having said that, is there a particular route that you would recommend or a direction you'd point someone like me in? Highly grateful for Bruces advice above regarding the HELOC but I've also seen the Home Equity Refi's and several others. Seems there are Pros and Cons to both (interest rate variability, repayment terms, etc), but being so green at this, I'm feeling a little like a deer in the headlights.

    Thank you again and I look forward to hearing back from you!

    Steve

  • Rental Property Investor · Stewartsville, NJ · Member since 2016 · 418 posts · 280 votes
    4y

    I agree with @Bruce Woodruff. If I were in your position, I'd get a heloc, but an STR, and refinance later.

    I was a little hesitant to move foreward with our first property.  What helped me get over it was saving up a large amount of cash prior to purchasing to handle anything unexpected and made me sleep at night.

    Hope that helps.

    Mike

  • Real Estate Consultant · Denver, CO · Member since 2021 · 661 posts · 389 votes
    4y

    @Steve Uekert You are thinking in the right direction, the best ROI seems to come from owning STR. The book and podcast mentioned by @Luke Carl well worth your time. Florida is a great place for STRs and most coastal areas welcome them. Be sure to check zoning and HOAs before buying with the intent to do a VRBO/Airbnb-type service. A big benefit to you is that if you purchase an STR near you, you can use the income from the property to offset your W2 income IF you manage it yourselves and put in more hours than anyone else. This is called "material participation". This makes the property an active investment, a business investment like any hotel-type property. A HELOC (home equity line of credit) is a good way to come up with a downpayment. And, don't forget that when you find a property to purchase, take advantage of the tax benefit of cost segregation in the first year if possible. This will give you some solid tax benefits and cash flow right up front.

    Someone else mentioned the Smoky Mountain area as good for STR as well. It is a bit far for you to be able to claim you materially participate but you may want to contact the woman and discuss her experience. I love the Smoky Mountains and visited many times years ago before it became so crowded with tourists. It is especially spectacular in the fall.

  • Rental Property Investor · Clarksville, TN · Member since 2016 · 1k+ posts · 1k+ votes
    4y
    Quote from @Bruce Woodruff:

    Get a HELOC on your paid-off house and buy a rental. Then Refi that and repeat...

    I know that sounds incredibly simple, but there ain't a whole lot more to it.....

    @Steve Uekert

     This, except I vote for cash out refinance.

  • Investor · Fairfax, VA · Member since 2015 · 1k+ posts · 796 votes
    4y

    Heloc is a no brainer.  You need to keep your existing low rate because if you refi you will lose that rate.  Having access to 75% of your equity in your home to me is finance 101.  75% of your $550,000 home means you will have access to just over $400,000 dollars.  Heloc rates are running about 4.5%.  Now get to work on that Heloc!

  • John UnderwoodPro Member
    Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes
    4y
    Quote from @Bruce Woodruff:

    Get a HELOC on your paid-off house and buy a rental. Then Refi that and repeat...

    I know that sounds incredibly simple, but there ain't a whole lot more to it.....

    This is what I would also recommend. 

    There is good debt and bad debt. Don't be afraid of good that allows you to make more money.
  • Member since 2022 · 4 posts · 3 votes
    4y

    Hi Steve, I'm also a newbie investor and found that going to my local investor meetup (Central Florida Realty Investors Association - CFRI) has been the best education as far as advice and tips, plus a great opportunity to meet seasoned investors in the Orlando area. They are always willing to share their thoughts and experiences. Many of them have STRs, and there's even a meetup specifically for STR investors every month where you can learn so much. I highly recommend it. Hope to see you there!

  • Bonnie LowPro Member
    Lender · Asheville, NC · Member since 2016 · 1k+ posts · 1k+ votes
    4y

    I would look into taking out a HELOC on your current home since you have a ton of equity sitting there and could take a substantial HELOC and still also leave substantial equity in your primary residence (insulating you from a downward market.) The HELOC funds can serve as your down payment AND a vehicle to massively accelerate mortgage paydown (and even paying off the truck) on the new STR property. To do that, I strongly recommend the Shred Method. Google it or listen to podcasts that feature Adam Carroll who is the founder of the Shred Method. It's also sometimes referred to as an Australian Mortgage. It's very do-able and complementary to your already frugal and FI-focused lifestyle. You have a lot of options and are positioned to do very well so good luck to you!

  • USA · Member since 2014 · 119 posts · 102 votes
    4y

    As a self identified Super Rookie, I would suggest *NOT* rushing in to things. It is good to be excited and motivated, people are here to push you to action. But give yourself the time to learn, strategize, make a plan, and act on it. Especially given today's market conditions. You have time to figure things out.

    That being said, @Bonnie Griffin Kaake gave some stellar advice. IMO a HELOC is best used for short term deployments, to get access to quick, short term cash infusions. Like a hard money lender but substantially cheaper for your own acquisitions.

    STR is "saturated" everywhere, meaning it is a buzz word everyone is frothing about that surged to the frontlines even when compared to just 2-3 years ago. But what if you spent the time to REALLY understand the STR opportunities in your back yard? Then lazer focus on that, and when you find the right opportunity (location, price tag, income, expenses) you are equipped with your HELOC to take it down. With material participation + cost segregation / bonus depreciation + first year's income, you could be well into paying off that HELOC ASAP (to then go deploy again). For more information on that, check out "Tax Smart Real Estate Investors" on youtube, and find videos tagged with short term rental loophole (many of which can be found in the playlist "The Real Estate CPA Podcast"). You'd ultimately need to connect with a CPA to make sure you are executing this correctly, because there are a lot of steps. But remember, you have time to get your ducks in a row!

    Another strategy I have heard people use, is to use a HELOC not for the down payment, but for a full blown cash offer. People were doing this as a way to win bidding wars, but nowadays with price reductions and buyer financing contingency cancellations, you can try to leverage your "sure thing" cash offer to get a discount on the property. Then, after closing, you use delayed financing to immediately turn around and get a long term mortgage to pay off (most) of your HELOC. Check in with lenders to learn more about the practical aspects of doing this.

  • Don KonipolBusiness Member
    Investor · The Woodlands TX / Avon, CT · Member since 2009 · 6k+ posts · 10k+ votes
    4y
    Quote from @Steve Uekert:
    Quote from @Don Konipol:

    So, you have a pretty common misunderstanding; you don’t distinguish between “good” debt and “bad” debt.  Bad debt isn”t actually bad, rather it’s unproductive, and can be bad if overused, or abused.  This is debt taken on to purchase DEPRECIATING, non income producing assets, like cars for personal use, vacations, food, clothing, etc.  Most credit card debt, auto loans, personal loans used for consumer purchases fall under this category.

    The “good” debt isn’t actually good, rather its productive.  This is debt that help you acquire assets that either APPRECIATE in value, throw off income, or better yet do both.  So for example a commercial building with a class A tenant paying a NNN rent of $120,000 a year acquired for $800,000.  But you only can come up with $200,000.  You borrow the other $600,000 secured by the property.  In 5 years you’ve collected $400,000 cash flow over your note payments; paid down you’re loan from $600,000 to $550,000, and the value of the property increased from $800,000 to $1 million.  Now these deals are rare, and may not exist in this low interest rate environment, but they do happen.  And you can see that taking on the debt was a good idea.  

    In any case, once most investors reach a certain level of wealth, which differs for each person, they either eliminate debt all together, or, better still, they only incur debt for which they have no personal liability.  

    However, if someone is so uncomfortable with debt that they can’t emotionally separate debt for investment from debt for consumer items, than they’re probably better off limiting their expectations at to the beneficial aspects of real property investing.  There will still be some benefits such as cash flow and inflation hedge, but the major benefit, leverage, will be eliminated and it will take 30 years to accomplish what can be done in 10 utilizing moderate debt with a moderate degree of risk.



     Hi Don!

    I'm planning on responding to everyone, but wanted to take a moment to respond to this post as I think you got to the heart of some of the feelings I've had since I began thinking and researching this business.

    Yes, I've been uncomfortable with debt for most of my life due to seeing debt ruin people around me. However, I'd like to think that while I'm uncomfortable with debt, that I'm not afraid of it as long as it most definitely qualifies as the "good" or "productive" debt. In fact, my wife and I have had a lot of discussion about this and one of the first things we talked about what about risk and how we're going to have to get comfortable with it.

    We're not risk averse, but we've definitely gotten comfortable and are willing to step out in faith. Having no debt is great, as long as you have the income or wealth to be able to retire without having to sell everything to live. And right now, I feel that's where we'd be at. So I'm more willing than ever to embrace the right kind of debt.

    Having said that, is there a particular route that you would recommend or a direction you'd point someone like me in? Highly grateful for Bruces advice above regarding the HELOC but I've also seen the Home Equity Refi's and several others. Seems there are Pros and Cons to both (interest rate variability, repayment terms, etc), but being so green at this, I'm feeling a little like a deer in the headlights.

    Thank you again and I look forward to hearing back from you!

    Steve

    Residential property, imo, is priced too high and returns too low, with a lot of risk of short - intermediate term price declines.  I invest mostly in commercial property, and although prices seem high they actually have a much better cash flow.  However, I’ve been wrong as often as I’ve been right about price movements, so it’s always a “best guess” , at least with me.  I buy only when I find or am able to negotiate a good to excellent price, i.e., under “market” by a good amount, or property that has some extra kicker where the chances of appreciation in price are significantly greater than the general real estate economy.  
    If I just wanted to buy real estate at market value I would just buy into an exchange traded REIT or REIT mutual fund or ETF as a diversified portfolio of REITs should match inflation over the long term and provide increasing dividends. You won't get rich, or learn about investing in individual properties, but unless you get compensated for the added risk and effort, in the way of added returns, why do it?
    This is a business, or more correctly an investment arena, where everyone thinks they’ve purchased a great below market price deal, and 95% have paid market price, they’ve just miscalculated the “adjustments” to the “comps” they’ve priced out, or the appraiser has.  However, for those able to hang on through the downturns, real estate investing is very forgiving, with long term appreciation not only bailing out investors on some dubious purchases, but often resulting in large capital gains through dumb luck.  I’ve had my share of luck myself.  For those of us addicted to real property investing, we must love every aspect of it.  My suggestion is that if you find you don’t love it, then invest passively through a REIT, private fund, or syndication.  

    Private Mortgage Financing Partners, LLC
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