Back to BP 4 years and 5 properties later

Member since 2023 · 14 posts · 12 votes

Hey Everyone,

I originally used Bigger Pockets about 4 years ago when I was looking for my first property, but haven't been active since. In that time, I've scaled up to 5 properties including a house hack, 3 small multifamily LTRs, and now working on launching my first STR with a partner. I live in Chicago but invest in Indiana.

I want to get more active here again because although I have learned a lot of valuable (and expensive) lessons, I know I have a long way to go. I'd love to connect with investors of any experience level, my areas of focus are small multifamily, deal analysis, and financial planning.

Thanks all,

Grady

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Jodi Taylor

Investor · Chicago, IL · Member since 2020 · 35 posts · 25 votes

Hi Grady! Sounds like we are in the same boat here. I haven't been very active on BP lately, have around the same number of properties, and focus on the same types of projects. Crazy! Yet, I'm sure there are many of us. Feel free to reach out to me anytime.

@Toni Husbands If you need help finding the meetup groups, don't hesitate to reach out to me. I can help you find them and help you find other networking mechanisms specific to the Chicagoland area. @Aaron Zimmerman would be even more helpful than me. He's much better about networking than I'll probably ever be haha...

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Ky Perry
Member since 2025 · 47 posts · 31 votes
1y
Hey Grady, congrats on building up 5 properties — that’s inspiring to see. I’m new to real estate and just getting started, so I’m trying to learn as much as I can from people who are ahead of me in the game. Really cool that you’ve done a mix of house hacking, small multifamily, and now STRs. Would love to connect and follow along with what you’re doing.
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Sean GrahamBusiness Member
Investor , CPA · Detroit, MI · Member since 2016 · 583 posts · 248 votes
1y
Welcome back, Grady!
Happy to connect with you.
Also take a look into the STR Loophole!
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Aaron ZimmermanBusiness Member
Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
1y
@Grady Schmidt - welcome! I'd encourage you to go to some local meetups, listen to the straight up Chicago investor podcast, and stay active on BP. Feel free to pm if you'd like to connect and I'd be happy to point you in the right direction for some resources.
[email protected]
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Toni Husbands
Investor · Chicago, IL · Member since 2017 · 16 posts · 1 vote
1y
Hi Grady,
I'm in a similar boat. Haven't been active on the forums in a few years but have been steadily investing. We're also trying to setup a STR and I'm looking for local meetups. I primarily invest on the south side. Happy to connect.
0 Reply
Nadeem Alamgir
Real Estate Agent · Member since 2023 · 831 posts · 577 votes
1y
Hey Grady, congrats on building up your RE portfolio up to 5 properties. Welcome to BP!
0 Reply
Jodi Taylor
Investor · Chicago, IL · Member since 2020 · 35 posts · 25 votes
1y
Hi Grady! Sounds like we are in the same boat here. I haven't been very active on BP lately, have around the same number of properties, and focus on the same types of projects. Crazy! Yet, I'm sure there are many of us. Feel free to reach out to me anytime.

@Toni Husbands If you need help finding the meetup groups, don't hesitate to reach out to me. I can help you find them and help you find other networking mechanisms specific to the Chicagoland area. @Aaron Zimmerman would be even more helpful than me. He's much better about networking than I'll probably ever be haha...
1 Reply
Toni Husbands
Investor · Chicago, IL · Member since 2017 · 16 posts · 1 vote
1y
Hey @Jodi Taylor I would any resources you have. I am most flexible during the day, while my kids are at school. Please share any info you have. Thanks!!!
0 Reply
Jodi Taylor
Investor · Chicago, IL · Member since 2020 · 35 posts · 25 votes
1y
@Toni Husbands I'll send you a private message :)
0 Reply
Grady Schmidt
OP
Member since 2023 · 14 posts · 12 votes
1y
@Ky Perry thank you! would love to stay connected, let me know how I can help as you get started
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Grady Schmidt
OP
Member since 2023 · 14 posts · 12 votes
1y
@Aaron Zimmerman appreciate it, I make sure I go to at least one local meetup in the each month. I'll message you, would love to hear what the best ones are.
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Grady Schmidt
OP
Member since 2023 · 14 posts · 12 votes
1y
@Toni Husbands @Jodi Taylor thank you both! Would love to connect since we're all in the Chicago area! I've been to a decent amount of local meetups but always looking for more chances to learn.
0 Reply
Paul De Luca
Real Estate Agent · Chicago, IL · Member since 2018 · 1k+ posts · 1k+ votes
1y
@Grady Schmidt
Welcome back! I'm a house hacker in Chicago and mostly work with buyers/sellers of 2-4 unit properties here.
Where do you invest in Indiana? If there's anything I can do to help feel free to PM me directly.
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Grady Schmidt
OP
Member since 2023 · 14 posts · 12 votes
1y
@Paul De Luca thanks for the message! where do you invest in Chicago?
All of my properties are in NW Indiana, basically between Chicago and South Bend
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- Paul De Luca
  Real Estate Agent · Chicago, IL · Member since 2018 · 1k+ posts · 1k+ votes
  1y
  Quote from @Grady Schmidt:
  
  @Paul De Luca thanks for the message! where do you invest in Chicago?
  All of my properties are in NW Indiana, basically between Chicago and South Bend
  
  Nice! Berwyn and NW side of Chicago for me (Belmont Cragin & Portage Park)
  0 Reply
Eudith VacioPro Member
Real Estate Agent · Chicago & NWI · Member since 2015 · 860 posts · 521 votes
1y
Hey Grady!
that is amazing, where in NWI do you invest? I'm from Chicago but have properties in East Chicago, Indiana & Gary, IN :)
0 Reply
Caleb Brown
Real Estate Agent · Kansas City · Member since 2018 · 4k+ posts · 3k+ votes
1y
Nice job! Welcome back to BP
0 Reply
Dustin Boots
Member since 2024 · 6 posts · 1 vote
1y
Hey Grady. I'd love to connect. I'm new to the game myself. Trying to get my investment career rolling from California. Myself and a couple Tennessee partners looking to start our journey. I've spent a fair amount on BP and reading some David Green books. Excited to get rolling.
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Arman AhmedPro Member
Real Estate Agent · Columbus Cleveland Dayton, OH · Member since 2024 · 2k+ posts · 924 votes
1y
@Grady Schmidt
Congrats on scaling to 5 properties—that’s solid progress, especially mixing in LTRs and now moving into STRs. I’m also focused on small multifamily and invest in the Midwest, so it’s always good to connect with others on a similar path. Curious—what’s been your biggest lesson learned so far jumping from LTRs into STRs?

[email protected]614-418-6081
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Drago Stanimirovic
New to Real Estate · Miami, FL · Member since 2024 · 1k+ posts · 455 votes
1y
Welcome back, Grady! Scaling to five properties including a house hack, multifamily LTRs, and now jumping into STRs, huge respect for the progress. Investing in Indiana from Chicago is a smart geographic play, and those lessons (even the expensive ones) are what sharpen your edge.

Sounds like you're in a great position to both learn and add value here. Looking forward to seeing your next moves, especially how that STR rollout goes.

Drago
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Grady Schmidt
OP
Member since 2023 · 14 posts · 12 votes
1y
@Eudith Vacio - my NWI properties are spread from East Chicago to South Bend. I actually think we may have met at one of your Saturday morning meetups a couple months ago. thanks for reaching out on here, would love to stay in touch

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Grady Schmidt
OP
Member since 2023 · 14 posts · 12 votes
1y
@Dustin Boots - very exciting! keep me posted on how things go

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Grady Schmidt
OP
Member since 2023 · 14 posts · 12 votes
1y
@Arman Ahmed thanks for reaching out! The STR isn't even launched, so I can't answer the question yet. We're renovating now, and this one is a partnership with another guy who has a couple STRs. So he's going to do the management while I'm along for the ride trying to learn. LTRs are much more of my thing at this point
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Jonathan KlemmBusiness Member
Moderator
Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes
1y
Welcome back @Grady Schmidt! Sounds like you are coming up for air after an incredible dive!

Please share more details about the journey! How come you chose Indiana over Chicago? Is your househack in the city?

I know @Eudith Vacio above is also a fan of that Indiana market
[email protected]
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E.J. McCaffrey
Member since 2025 · 194 posts · 140 votes
1y
Welcome back to the group.
Real estate can be incredibly rewarding, but it comes with its share of risks, ranging from lawsuits and liability exposure to unexpected creditor challenges. Without proper safeguards, your investments and personal assets may be at risk. Putting the right legal and financial structures in place can help protect your wealth, minimize litigation exposure, and restrict access by potential creditors. In fact, strong asset protection can often improve your leverage in negotiations or legal matters, leading to more favorable outcomes.

To navigate these complexities, it’s wise to build a reliable team of knowledgeable professionals. This typically includes a seasoned tax advisor with real estate expertise, along with an asset protection attorney who understands both your investment strategy and risk tolerance. With the right guidance, you can create a strategy tailored to your goals, helping you save time, reduce stress, and preserve wealth as your portfolio expands.

Smart investing isn't just about acquiring the right properties, it's also about securing what you build. Wishing you continued success, growth, and peace of mind on your investment journey!
Disclaimer: This message is for informational and educational purposes only and should not be considered legal, tax, financial, or investment advice. No attorney-client, fiduciary, or advisory relationship is created by this communication. Always consult with qualified professionals familiar with your specific situation before making any decisions.
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Micah White
Real Estate Coach · Chicago, IL · Member since 2020 · 171 posts · 64 votes
1y
Welcome back! Sounds like you’ve made a ton of progress since your first BiggerPockets run — congrats on scaling to 5 properties and branching into STRs, that’s huge. I’m also focused on small multifamily here in Chicago, so I can definitely relate to the “valuable (and expensive) lessons” part.

Would love to connect and trade notes, especially around deal analysis and financial planning — always good to sharpen the numbers with other investors. Out of curiosity, what’s been your biggest lesson from shifting into STRs compared to LTRs?
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Terrance HillPro Member
Realtor · Memphis, TN · Member since 2010 · 425 posts · 117 votes
1y
Welcome back, Grady! It's awesome to see how far you've come in just a few years — 5 properties and your first STR venture is impressive. Scaling from a house hack to multifamily and now STRs gives you a ton of perspective that's super valuable to share with others here.

Investing out-of-state in Indiana while living in Chicago definitely shows you’ve built a good system. I’m sure many members will benefit from your insights on deal analysis and financial planning. Excited to see you active again and hear more about your journey!
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