What is the regulation environment? 

Also, as I am in CA, it would be impractical to be "boots on the ground" for an extended length of time to visit properties and  attend numerous auctions in person.

You should also familiarize yourself with landlord-tenant laws and regulations specific to the market you choose.

Research the local regulations.

To keep up with relevant advances, I read numerous publications each week.

I've reached out to the City of Winston-Salem to gain more information on tiny house regulations since there was not much to be found online.Thanks!

Lenders face far more regulations when lending on owner occupied properties which may limit your options.

For numerous reasons we decided to sell, and received at offer from the Church that was one of the occupants, for a price equal to appraised value.  

Hi Jacob,I agree with Bruce, if you can show up or call the HOA to find out their stance on 30 day rentals this would help you figure things out better.Ask to see the HOA's Bylaws and CC&RRs (Combined Community Rules & Regulations) to see if there is language that allows rentals/leasing (without restriction).If there is, determine what the criteria is for amendment changes to the CC&RRs.

Definitely look into STR regulations in any area you're researching.