Have others bet on cities like Cleveland, Milwaukee, Minneapolis, etc given the relatively low climate threats in these areas?

@Troy Scottaline a safe bet is you can get somewhere from 6-8% cash on cash return after all expenses are paid on your investments.So if you want to live on over $100,000K per year and do nothing but manage rentals or manage a property manager you will need well over $1,000,000 to invest.

Assuming this was on platform and it must have been. 

Find a faith community that welcomes you - and I'd bet that all will. 

The issue with Airdna and other platforms is they take the aggregate of all the nightly rates of the high end and low end property's  together and come up with your "average" rate & occupancy.

Your best bet is to try areas outside of the 285 perimeter or go direct to seller.

I'd bet there is and therefore there is no 'housing shortage'.

She is a fantastic estates and probate attorney here in town and I bet she can help save the deal and get you what you need.

If your goals are cash flow only (as in you want mail box money to live off of), then finding that cash flow market would be your best bet.

Hire a professional photographer for pictures, find a good cleaning team and handyman, make sure you are comfortable with whatever management platform you will be using to communicate with everyone.