I was reading another thread on BP about the difficulty of evictions in Cook County which definitely worries me a little bit, but I guess that just means very stringent tenant screens are a must.

I've lived abroad for a decade and negotiating is a part of daily life; from buying vegetables at the market to a new washing machine.

The dwelling unit is a non-housekeeping furnished room or a unit without cooking facilities; or5.

Hey @jordan - In Illinois and specifically Chicago / cook county you never know what is going to happen with property taxes. 

google steve cook.

.)- Tenant operations that may be harder to insure (cooking, woodwork, manufacturing, etc.)- Construction of buildings/fire protection that may impact the insurance (frame construction in a non-hydranted area or one with distant fire depts)I echo the posts that emphasize the importance of an experienced real estate attorney. 

In addition Cook County has set up few new classification for properties that are converted to STRs. you can visit the assessors website to find oit more.

I am usually working till about 9:30 in time to cook diner, watch a short Netflix show, and hit the hay. 

You will find hype, unrealistic expectations, and half-cooked advice (sure, like mine).The BP books are so so, not great.

I went and seen it today. 1/4 of the rear fascia is gone, some of the soffit has vegetation growing on it, the shingles looks “okay”, the wood under the shingles are planks, the crawl space in the attic is very small, the air handler will more than likely need to be replaced, because of mold concerns I would budget for the duct work as well, but I would wait for the a/c guy to look at it.