I really wanted to convert the residence to a rental property, but everything I have heard about doing so in Cook County has been very concerning.

Put a sign up in the corner store.And I would rethink your concern about 'rough areas'...

Hi Joshua,To gain a clearer understanding of the overall condition of the home—including plumbing, electrical systems, HVAC, and the roof—and to identify any major issues such as asbestos, water damage, mold, foundation concerns, or wood-destroying insects, I strongly recommend having the prospective properties thoroughly inspected.

Also concerning, I just looked at zillow post and the pictures are very grainy and unflattering, even though they should have access to the nicer photos (I have had these for years, see below)..I've also been getting lots of calls form companies wanting me to sell my house.

Majority of banks, credit unions, and hard money lenders are cutting back.

My biggest concern is the basement.

Typically those purchasing cash aren't inspecting every home, they're walking it or having their go to GC walk it and already know what they see that may be a concern. 

People’s Republic of Asheville is more concerned with STR regulations than people living in boxes on the streets.

It does not mean that they are not legit, but it is a concern. 

Some have done owner financing with an agreement to pay all interest and equity splits when the home sells others have done it where they do a quitclaim adding their name onto title with the seller so once rehab is done the seller can't try and cut you out of the deal.