So the restriction only allows it to be rented out for half the year correct?  

Find out all you can about assets held by the PM and her business.

Or, when the lawn boy goes to get lawnmower gas in his uninsured car and wrecks into someone on your business.

Are you able to turn it into an AirBnb or is that not allowed or too much trouble?

Once everything is set up, you'd do everything for your business through your LLC, including paying bills and taking payments.  

Not sure if its a regulation issue or what it is, but I've only been able to even entertain the idea of doing business with HMLs on the MN side of the border. 

Hello, thank you for your response. my main goal is financial freedom, I own a corporate training business and have been able to save money, but now I would like it to start working for me through smart investments.

It is very challenging to get your AirBnB license unless you are renting out YOUR UNIT or you do 25% of your units if you have over 6 units or something along these lines.The only way I'd advise STRs in Chicago would be if you are going operate a business to scale and had the resources/local knowledge to do so.I'd actually highly suggest Michigan because there is WAY LESS restrictions.

Please contact them as we are not allow to self promote. 

That allows you to use the appreciated equity as your future down payment source.