People don't use Airbnb much in my area.

Why do I need to tell people where to go and eat when they have Google and Yelp?

I think I would recommend people start class b but I recognize the challenges to get the numbers to work.  

I’ve been in this space for a long time, coaching and investing, and I love helping people get started.

Otherwise perhaps your winter people will pay $500 extra if your cap is $500 and that is not what your competitors will be doing. 

I wouldn't accuse people that write listings to be knowledgeable in insurance. 

I’d recommend listening to the straight up Chicago investor podcast for local information, going to the variety of meetups that are in this great city, and meeting a lot of the people posting here. 

I'm just beginning but am considering a bigger commitment in the next five years or so by accessing some or even all retirement funds to buy a building (I'm sure people have thoughts on whether or not that is a good idea!).

My father did this in Portland on two properties, for elderly people I think. 

The five people you spend the most time with will influence you.