I'm Just Getting Warmed Up

[Matthew W.]

Greetings Bigger Pockets Community!

I'm a technology consultant from Chicago that's been lurking for years (as time allows) but haven't posted previously and haven't bought an investment property myself yet.

My research into RE investing is extensive, but actual investment experience is limited. I've been on the lending side briefly several years ago, and have participated on crowdfunding sites like Lending Club and GroundFloor for many years, and REITs like Fundrise for a couple years. Nearly 30 years ago - in college - I property managed the multi-family I lived in for just over a year, and I've dealt with the problems related to my primary residence, which I own, but that's about the limit of my experience. 

Very busy work schedule so I have limited time available, so looking for more passive opportunities for now. Don't really think Chicago is the market I want to invest in at the moment, and learning about out of town opportunities (also because that would force me to have property management in place). Considering Indianapolis and open to other places that aren't too far.

Looking forward to being active and actually getting to the point of buying an investment property or two, or partnering with someone more experienced on a deal. 

[Melissa Justice]

@Matthew W.,

Welcome to BP!

Given your time constraints + tech consulting schedule, passive or semi-passive makes a lot of sense. Many in your position start with out-of-state turnkey SFRs where management, rehab, and leasing are already in place.

You’re spot on about Chicago - tough cash flow and heavy management. You may also want to look at other parts of the Midwest and Southeast where fundamentals are strong: lower entry prices, stable tenant demand, and better cash-on-cash returns.

Common path I see work well:

1 turnkey rental to learn the ropes

Professional PM from day one

Conservative leverage

Focus on boring, repeatable markets

Some turnkey operators are also offering incentives right now (rate buydowns, rent guarantees, closing cost credits), which can reduce friction on a first deal.

Always happy to chat more about what's worked for other investors. Best of luck!