I’m specifically asking about eligibility for the higher return rate offered to Stessa Pro members when using Stessa Cash Management.

Based on what you've said here, I'd probably rent it out as-is for a couple years and then 1031 in to a higher quality area. 

You STRs tend to be a little higher end and guests have higher expectations.

STRs can bring great returns but are higher risk and more hands-on, like small-cap stocks, while long-term rentals are stable and predictable, like large-cap investments.

As an new investor you should consider which factor is higher risk - proximity or market dynamics. 

Some of our borrowers are focusing on 4 bed 2 bath section 8 to push those numbers even higher.

Or if you want to swap higher returns for lower maintenance you can look in to FIG (fourplex investment group_.

BRRRR deals can be trickier to come by in these spots due to their higher demand, but the way to go is to build a solid team with local connections who can share insights and bring you deals!

Chicago cap rates are actually much higher then other comparable sized cities.

Many voucher holders also work and so sometimes they will have a higher amount to spend than someone who doesn’t work because they can pay up to a % of their net income from the HA’s calculations, often 30-40%.