My time is very limited with my full-time job, and feel it might be best if I have all the information in one place and a resource along the way. 

Here goes… If you are not a Real Estate professional, and your high income is from a different field, you cannot deduct “Passive Income” Losses.

(income or loss?)

Based on my very limited research the west side is probably the best, however many of the multi families are in the downtown area near the border and in less desirable areas.

If there is an HOA it has to be registered with the state (in my experience which is only TX, CA, CO) and the by-laws should be recorded at the county recorder's office, again in my limited experience this is always the case. 

By "professional landlord changes things" did he mean that you would now be considered a real estate professional and therefore eligible to take advantage of real estate losses vs a non-real estate professional?

This almost entirely offset the loss in income from selling the buildings.

Seems that as long as I build the cost into my numbers up front it'd be a good way to limit my exposure to tenant struggles and take advantage of the company's experience and knowledge of the market.

Looking to explore options for owner occupant lenders outside the conventional limits that borrow in Chicago to high credit/income individuals with under 20% down.

Would you sell at a loss?