Quote from @Moe Sidd: Highly suggest reaching out to the FIRE Realty Team, they have a bunch of agents who specialize in investment properties.Thank you! 

For a renovated Pilsen 3-flat, somewhere $10–13K.Also check rent comps for new construction Woodlawn: if more buildings deliver, you may be competing through concessions or slower lease-ups.If it were me and I wanted a smoother first few years, I’d choose Pilsen unless the Woodlawn building is truly special or priced with enough cushion.Happy to run the numbers with you if you want to stress-test both deals, Chicago is all about underwriting the next tax bill, not the current one.

I recommend speaking with a local lender who specializes in investment properties, rather than a big-box bank.

Insurance companies work with specialized temporary housing providers to place displaced residents, rather than providing housing directly.

Winter’s around the corner, and I know the rental market slows down in a lot of places.I’m curious how everyone handles vacancies this time of year — do you offer move-in specials, flexible lease terms, or just ride it out until spring?

Standard insurers may offer coverage, but you may need to pursue specialized policies or a state-assisted plan if you face rejection. 

Find an investor friendly agent that specializes in house hacking.

I also specialize in short-term rental investment sales on HHI.

You’re in a great spot with lots of options.From a tax perspective, your STR could qualify as a non-passive business if the average stay is under 7 days and you manage it yourself.That opens the door for a cost segregation study and big bonus depreciation write-offs often opportunities that many CPAs who don't specialize in real estate miss.Like others have mentioned above, you can’t do a Solo 401(k) with just W2 income, but if you treat the STR as a business and pay yourself for managing it, that income could qualify, giving you another powerful retirement planning tool.Next steps: start by finding a tax strategist or CPA who really understands real estate and short-term rentals, and an estate planning attorney to protect what you’re building.

Real Estate is a highly specialized tax environment.