(I assume he owned a convenience store or something)  for $7,000. 

Kinda like a slotting fee in a grocery store?

Building sits on a corner and all basement windows are above ground.

For curtain rods, charge him replacement costs; for curtains, go to a thrift store and see if you can find some that work and charge him depreciated value. 

Rate cuts could spur inflation again, which I think most people who go to the grocery store etc. really do not think its getting that much better and home prices are not falling dramatically. 

July 1 to Aug 15 STR revenue will cover the mortgage for the year provided that we spend that time staying with family and/or on a low-ish budget vacation.I'm not suggesting you move to this forgotten corner of the country, but look at a solid vacation rental market.

If you have to evict in Chicago, don't cut corners, and hire an attorney. 

Even just a box store H&R Block type of professional if you don’t already use one to help maximize your deductions and write-offs from the real estate.

It sounded like you've turned a corner on this unit's performance. 

If it is truly a detention pond, the purpose of it is to temporarily store storm water.