New investor seeking mentor or like-minded individuals

New to Real Estate · Chicago, IL · Member since 2020 · 10 posts · 19 votes

Hello everyone,

I am new investor who is seeking to begin my real estate journey. I am a recent veteran who is currently a software engineer and would like to acquire my first rental property within the next 3 - 6 months. I recently relocated back home to the southwest suburbs of Chicago, IL and I am seeking like-minded individuals or potential mentors who are willing to meet over lunch or coffee and discuss their experience and provide some guidance. If you are interested in connecting, please tag me here. Thank you, I look forward to connecting with you all.

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Jaycee GreenePro Member

Real Estate Consultant · St. Louis MSA · Member since 2024 · 3k+ posts · 727 votes

Quote from @Jovany Espinoza:

Thank you for the replies and warm welcomes. I look forward to connecting with you all.

A little bit about what I am striving for; I am looking to purchase a single family home preferably under $120k, anywhere within the midwest region: Chicago, Michigan, Ohio, Wisconsin all work for me.

One strategy I am interested in exploring is single family homes that qualify for Section 8 housing. I've been hearing more and more about Section 8 rentals being a big thing today. Not only can it provide you some stability via consistent payment (gov voucher) but vetting tenants and getting qualified people can potentially mean long term tenants. If anyone has experience in single family homes with favorable methods (low down payment, seller financing) please send me a connect. I do have some consistent capital but I am seeking a mentor or someone I can build a friendship/relationship with, while on this endeavor.

Once again thanks for replying on my discussion, I truly appreciate the acknowledgement and support.

@Jovany Espinoza So, something like this in Columbus: 698 S Wayne Ave, Columbus, OH 43204?

[email protected]

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Seth McGatheyBusiness Member
Real Estate Agent · Milwaukee WI · Member since 2024 · 321 posts · 255 votes
1y
Thank you for your service and welcome! Always exciting to be getting started!

I am also in software, (QA automation engineer), and also live in the Midwest, (Milwaukee). Since we are over an hour from each other, I don't know if it makes sense to meet up just for coffee unless we are already in each others area, but I would be more than happy to connect virtually and chat more about your goals and plans and see how I can help you strategize. (I am also a real estate agent and investor myself).

Best of luck on your investing journey!
[email protected]708-297-0996
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Joseph Bui
Lender · Nationwide · Member since 2023 · 362 posts · 237 votes
1y
Hi Jovany, I spent most of my working life in tech as an engineer and TPM. More recently I started focusing on real estate investing activities full time, flipping, long term holds, loans and marketing. Happy to help answer any questions or if you need help with financing.
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Aaron ZimmermanBusiness Member
Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
1y
Welcome to Chicago! I would recommend listening to the straight up Chicago investor podcast for local tips and attending local meetups.

I'm a former house hacker and real estate CPA in Chicago. I'm down for a phone or video call and happy to help you out. Feel free to PM!
[email protected]
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- Luke Thomas
  Member since 2025 · 11 posts · 7 votes
  1y
  @Aaron Zimmerman
  
  Hi Aaron!
  
  I am from the Lake Geneva area, which I'm sure you've heard about being from Chicago area. I'm 23 and recently bought my first property here, did a cosmetic rehab, and am currently house hacking with 2 roommates. I plan to take a HELOC out soon to fund my next rehab. If you would like to chat about anything in the future let me know, I'd love to get your insights on things!
  1 Reply
Paul De Luca
Real Estate Agent · Chicago, IL · Member since 2018 · 1k+ posts · 1k+ votes
1y
@Jovany Espinoza

What's your strategy for buying your first investment property? What's your buy box?

If you need referrals to help build your real estate team (lender, attorney, inspector, etc), feel free to PM me.
0 Reply
Jovany Espinoza
OP
New to Real Estate · Chicago, IL · Member since 2020 · 10 posts · 19 votes
1y
Thank you for the replies and warm welcomes. I look forward to connecting with you all.
A little bit about what I am striving for; I am looking to purchase a single family home preferably under $120k, anywhere within the midwest region: Chicago, Michigan, Ohio, Wisconsin all work for me.

One strategy I am interested in exploring is single family homes that qualify for Section 8 housing. I've been hearing more and more about Section 8 rentals being a big thing today. Not only can it provide you some stability via consistent payment (gov voucher) but vetting tenants and getting qualified people can potentially mean long term tenants. If anyone has experience in single family homes with favorable methods (low down payment, seller financing) please send me a connect. I do have some consistent capital but I am seeking a mentor or someone I can build a friendship/relationship with, while on this endeavor.

Once again thanks for replying on my discussion, I truly appreciate the acknowledgement and support.
2 Reply
- Jaycee GreenePro Member
  Real Estate Consultant · St. Louis MSA · Member since 2024 · 3k+ posts · 727 votes
  1y
  Quote from @Jovany Espinoza:
  
  Thank you for the replies and warm welcomes. I look forward to connecting with you all.
  A little bit about what I am striving for; I am looking to purchase a single family home preferably under $120k, anywhere within the midwest region: Chicago, Michigan, Ohio, Wisconsin all work for me.
  
  One strategy I am interested in exploring is single family homes that qualify for Section 8 housing. I've been hearing more and more about Section 8 rentals being a big thing today. Not only can it provide you some stability via consistent payment (gov voucher) but vetting tenants and getting qualified people can potentially mean long term tenants. If anyone has experience in single family homes with favorable methods (low down payment, seller financing) please send me a connect. I do have some consistent capital but I am seeking a mentor or someone I can build a friendship/relationship with, while on this endeavor.
  
  Once again thanks for replying on my discussion, I truly appreciate the acknowledgement and support.
  
  @Jovany Espinoza So, something like this in Columbus: 698 S Wayne Ave, Columbus, OH 43204?
  [email protected]
  2 Reply
Denise SuppleeBusiness Member
Realtor · Willow Grove, PA · Member since 2017 · 1k+ posts · 655 votes
1y
Hey @Jovany Espinoza welcome—and thank you for your service! I’m one of the co-founders of SparkRental. I’ve been in real estate for over 30 years and now run a co-investing group where we team up on deals and share insights.

We host regular Zoom calls where investors (new and experienced) connect and chat through what they’re working on. You’re more than welcome to join in. Next call is Thursday 7/10 3:30 pm ET

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Jacob Haddan
Member since 2025 · 9 posts · 2 votes
1y
Hey Jovany I'm a mortgage broker based in Colorado. I can possibly help you. Let's connect. My site is mortgageconsulting.group
0 Reply
Peter Falk
Real Estate Broker · Madison, WI · Member since 2015 · 118 posts · 60 votes
1y
Hi Jovany,
It has been a while since I had a section 8 tenant, but if you want to focus on that, when you settle on a market can contact the local organization that handles those vouchers (for example, in Madison, WI it's the City of Madison Dept. of Planning, Community and Economic Development and for surrounding communities, it is through Dane County Housing Authority.
Those groups can give you an idea on their demand and rental rates (as I recall based on bedrooms) and basics on housing safety standards you will need to meet as the Fed. Gov't wants to make sure they are spending money on safe housing.
As you said, definitely still screen all Sec 8 applicants. You really only want to consider their vouchers as income and make sure you want to rent to them beyond just qualifying on income (good housing history, etc.).
I like your idea of single family homes to rent as those are easy to have tenants pay all utilities and do snow removal and lawn care. Unfortunately, in the general Madison, WI area, we don't see a lot of single family homes for rent as the buyer demand and higher home prices make it less attractive. For some context, with MLS data, last year in Madison, the median sale price of a 3 bed, 1-2 bath home with under 2,000 sq ft above grade was $394,960 and average almost $419k and similar pricing in Dane County overall as buyers move out to surrounding communities in search of more affordable options.
Milwaukee is a big market I am not that familiar with as I live in Madison, WI, but if you decide you have an interest in Rock County, prices can get in your price range in places like Janesville and Beloit, WI, but still mostly above $120k (median sale price last year in Rock Co with that home criteria was $253k, but sales did take place in your price range if you end up in that area of south central WI. Happy to talk more specifically if you end up focusing more in my area. Good luck!
1 Reply
- Luke Thomas
  Member since 2025 · 11 posts · 7 votes
  1y
  @Peter Falk
  
  Hi Peter!
  
  I am from the Lake Geneva area, which I'm sure you've heard about being from Madison area. I'm 23 and recently bought my first property here, did a cosmetic rehab, and am currently house hacking with 2 roommates. I plan to take a HELOC out soon to fund my next rehab. I am very close to Janesville and Beloit as you mentioned. If you would be interested in chatting sometime, let me know. You seem like a ball of knowledge!
  1 Reply
Luke Thomas
Member since 2025 · 11 posts · 7 votes
1y
Hi Jovany!

I am from the Lake Geneva area, which I'm sure you've heard about being from Chicago area. I'm 23 and recently bought my first property here, did a cosmetic rehab, and am currently house hacking with 2 roommates. I plan to take a HELOC out soon to fund my next rehab. If you would like to chat about anything in the future let me know!
0 Reply
Crystal SmithPro Member
Moderator
Real Estate Broker · Chicago, IL · Member since 2014 · 2k+ posts · 1k+ votes
1y
Quote from @Jovany Espinoza:

Hello everyone,

I am new investor who is seeking to begin my real estate journey. I am a recent veteran who is currently a software engineer and would like to acquire my first rental property within the next 3 - 6 months. I recently relocated back home to the southwest suburbs of Chicago, IL and I am seeking like-minded individuals or potential mentors who are willing to meet over lunch or coffee and discuss their experience and provide some guidance. If you are interested in connecting, please tag me here. Thank you, I look forward to connecting with you all.

Consider yourself officially tagged. Feel free to reach out.
312-681-7487
1 Reply
Charles ClarkBusiness Member
Real Estate Broker · Milwaukee, WI · Member since 2020 · 306 posts · 209 votes
1y
@Jovany Espinoza

Hey, welcome and thank you for your service! 👏 It's awesome that you're taking the leap into real estate—your tech background will definitely be a strength. I'm not local, but there's a great community here and I'm sure some experienced investors in the southwest suburbs would be glad to connect. Wishing you the best as you kick off your REI journey—you're in a solid market with a lot of opportunity!

[email protected]414-719-6090
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Micah White
Real Estate Coach · Chicago, IL · Member since 2020 · 171 posts · 64 votes
1y
Hey, first off—thank you for your service and welcome back to the Chicagoland area! It’s awesome that you’re diving into real estate and looking to connect with others who can share experience and guidance.

I’m also involved in real estate investing around Chicago and working with folks new to the space. If you want to connect over coffee or just swap notes virtually, feel free to reach out anytime. I’ve found that building a network early really helps smooth out the learning curve and opens doors.

Looking forward to seeing your journey take off—let me know if I can help with anything!
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Kaila Epps
New to Real Estate · IN · Member since 2021 · 8 posts · 7 votes
1y
I plan to move back to Chicago in the next year or two and will definitely want to invest in real estate there, so I'm following this thread. Welcome back to the midwest! (I'm currently in Indy) :)
1 Reply
Micah White
Real Estate Coach · Chicago, IL · Member since 2020 · 171 posts · 64 votes
1y
Welcome, and thank you for your service! Exciting that you’re jumping into your first rental within the next few months — software engineers tend to have a great analytical approach to deal analysis, which will serve you well.

I’m also based in Chicago and focus on small multifamily and value-add deals. Happy to connect over coffee or a call to share what I’ve learned so far (the wins and the mistakes). BiggerPockets is a great place to find like-minded investors, and it sounds like you’re approaching this with the right mindset.

Tagging you here so we can stay in touch! @Jovany Espinoza
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