Do I sufficiently school up in the Chicago market and IL regulations and build a bit of a network here to start off, with the ease of seeing many properties first hand?

These are offerings under Regulation A+, which allow raising up to $50M in a "mini IPO".

I think you'll be hard pressed to find a city or town in Florida that regulates against a weekly rental,  but you will find a lot of HOAs that are against it, so I would look at your most popular places, check the local regulations, then when you start looking for property check the Association rules. 

(How often is the government right?) 

You did not mention where you are but all of Texas will probably do good unless the new government messes it up.  

Advertising what the public records provided by your local government is typical.

They should call it "renter control" since the landlord loses control of the property with the rent control regulations.

I would say most do relapse some time, as I have known drug addicts and witnessed it personally, There may be some government programs to help with the cash flow aspect of it.

The final example for the sake of this post could be failing to send in an award letter for SSI or other government entitlement benefits.  

Government, other than the President.