We would end up with an enclosed sump and a scar in the concrete floor around the perimeter.  

I suppose you know what the balloon payment is now, however most residential loans are NOT assumable and I read the ad as the seller selling as a "Subject-To" transaction as an all inclusive deed is a type of special warranty deed where the seller does not give clear title, title is subject to paying off the existing lien as agreed.

I would check the RLTO on the first item, that may not be allowed in Chicago.The refusing entry is addressed in the RLTO and the summary has to be included with every lease.If you are owner occupied under 6 units you are exempt from the RLTO but I always suggest every landlord use a RLTO compliant lease like the 35 page CAR one that includes everything you need

. (~4-6 bedrooms here).B-level: Similar criteria to A-level but without the custom built homes, 2-income families can afford to live here and raise a family, backyards for the kids, 1500-2000 sq ft houses (~3 bed/2-bath homes).C-level: Majority of houses under 100K, visual repairs needed in this neighborhood, 1200 sq ft average, houses close together, some properties worn down, grass not cut, porch awnings sagging, concrete stairs crumbling a bit.D-level: Struggling neighborhoods, garbage on the streets, bars on the windows, higher crime, crowded areas, downtown city area, wouldn't want to walk around here at night.F-level: War-zone, "get me outta here" property, makes you nervous to enter the neighborhood even in daylight.That's my basic approach when I think about properties and what areas make the most sense to invest in.

Section 8 compliant housing.

I am wondering if a landlord of a 3500sq/ft, 4unit, section 8 compliant property can program the furnace thermostat to a specific temp (say, 70 degrees) and tenants wouldn't be able to run the bill up?

Might want to google concrete counter tops and view what I see. 

This is a section 8 compliant home so I don't really was mess with the rents too much, at least til I get feel for landlording and what kind of tenants are currently there.

The most efficiently do this is to outsource that vital task to a consumer reporting agency (CRA) that specializes in background checks and here is why:  A CRA must conduct Fair Credit Reporting Act (FCRA) compliant background checks.

Fred Heller This is Ada.