People have found amazing deals in the worst of markets.  

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.

When I started working, I was like most people—brainwashed into thinking that putting money into a retirement plan was the right thing to do.

If there are people buying them, it's best to see how they're buying them. 

I have property at the edge of Lehigh U that I thought would be for students when I first started out there. i quickly realized that student housing, especially in the smaller school, is a totally different business with different expectations and requirements, not to mention yearly turnover and parent involvement.

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

Do a lot of people on BP have experience with this?

People are coming to Florida for fun, sun and something different than they have at home, your photos should get them excited.

As for some of the other things people have mentioned. 

I think most people would, so I'd definitely lean towards keeping it as a rental.