There is still another month in planned rehab, so nothing pressing, but would love any recommendations people have!

@Samuel Boyd I am not very familiar with the area but plan to be spending more time down there.

I'm under contract on a single family home in Chicago, and the rehab will include adding two dormers, so I'll need an architect to draft a full plan set for submittal to the City of Chicago Planning Dept.

The "peak" of the raised section is about 4" higher than the rest of the floor.

Good evening,I'm a landlord and have a tenant on the 2nd floor who has children.

Don't get me wrong, I love STRs, but if your place is average, you plan to keep it average, you may be better off just getting a long term renter and make out better. 

We have a building that is about 5000 sq ft (4000 first floor, 1000 second floor), we are trying to figure out the most optimal thing to do with it.

Try looking into zillow/Redfin and see what your potential rents you can get near the neighborhood by filtering the bedrooms/bathrooms of the intentional property that you are planning to buy.

You can compete with riskier stuff outside common buy boxes and in tertiary markets.If you aren't already licensed, is the plan to use a Realtor to make offers on your behalf, given it is already listed on the MLS, and then shop around for a buyer? 

I'm sorry the investment isn't working as planned but you have a commitment to uphold.