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.

My investor plans to turn this into a nice 4 bed home with the goal of selling between 250-275k What made you interested in investing in this type of deal?

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. 

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.

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

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? 

After hearing them explain it, my mind immediately started spinning and imagining all types of ideas to support some of my future real estate business plans.

The only reason I didn’t rip off the bandaid and raise rents the full $500 is because I planned to switch it to where the tenants will be paying for their own heat.