But I think the your point on this causing a business loss is what's going to be my biggest huddle.

@Sean Doyle - Toledo is the only city I operate in.

I navigate through cities and towns, identifying areas that are both friendly and challenging for STRs.

I have a client in Kansas City that does this.

I've lived here my whole life and have really seen a dramatic change in this amazing city. 

Funding the larger properties to start sounds like it will be my biggest challenge and I'm not convinced, yet, that I can't find the money out of my own pocket or find OPM to get a deal done.

Are you in the city or in a suburb, for example?

Then later on purchase homes with cash (single family homes), I would like to learn how to read the market and know where a state or city is thriving but also learn where it's not.

HOA fees, in particular, seem to be the biggest hurdle.

I sent an email to the city and received a long response.