Your carrying costs include mortgage, property tax, insurance, electricity, water, garbage, HVAC since it's summer and any HOA if applicable.Get a Prelim Title report $50 to $60 in most places.

. :)Also, judging by the specific issues you mentioned, buying and then selling would probably be better than buy and hold just due to the water in the basement....that could be a nightmare down the road.

Mainly, the systems implemented are fascinating (VA, automated offers, etc.)

It has no HVAC system and no insulation.

Water/Sewer rates I got from here (https://www.cityofchicago.org/city/en/depts/fin/su...).

Owning/managing an STR is not as simple or straightforward as standard rentals and to successfully run them you need to have good systems and procedures in place to sustain them.   

Hey Nick.My name is Mario,  and I help real estate investors to automate as much as possible their Deals acquisition process through the use of effective social media ads and a personalized system that will make everything work effectively.Think about it as a robot finding deals for you.Any question regarding marketing applied to real estate... ask Mario Nice to meet you everyone in the forum

It's a pretty unorganized system right now that I'm not particularly happy with - would also like to hear what others use....

Since my auto loan was originated by the dealership, I was in a loophole system that I did not have to be a member of the credit union to have the loan.

One thing to look at is the water and sewer... that's a large expense that would be good to get in the tenant's names if at all possible, especially if that's more typical of the area anyway.