Practical Tips for Managing PropertiesFinding Good Tenants: Screen thoroughly.

What new apartments are permitted around it...or 1/2 way thru construction, but not on the market.How do you become an expert or master it.....probably like any other skill...practice. 

No, it is inside of an HOA neighborhood but the current regulations only restrict rentals under 30 days stays.

Understand Chicago ZoningChicago’s zoning regulations vary by ward.

The area has certain advantages like shelter from regulation risk (pretty much as low as anywhere in the country if you buy in the approved STR tourist zones) and long term security (people aren't going to stop going to Orlando anytime soon). 

I don't see them ever reversing the regulations.

Remember your situation is unique so it's important to consult with a tax advisor or CPA to explore all available options and ensure compliance with tax regulations.

As long as there is no "healthcare" being provided (medicine, baths, etc) then it's not regulated by the department of health.

Educate yourself with resources like The House Hacking Strategy and practice analyzing deals using tools like BiggerPockets calculators.

Best practice is to keep one or two payments in reserve from the buyers down payment for such instances.