The various cities out here each have their own regulations restricting STRs and those regulations can and do change relatively abruptly.

It will depend on your state landlord tenant regulations regarding community rules which may or may not be the same thing as the lease.

Use some of the available tools out there to run high level analysis and then once you have a short list you can start engaging property managers, do more manual research on the existing booking platforms and/or pay for more expensive data to fine tune your analysis.Best of luck!

You can, however, use a VA loan to refinance an existing rental home you once occupied as a primary home.

@Mitchell Litam , the existing lease runs with the property until it ends, however make sure to read your state's landlord tenant laws, so you know how you can make changes once it comes up for renewal, how much notice you have to give them, etc.Water/electric bills in their names is a matter for their current lease and your utility company's policies.

All of those expenses and risks that you mention exist at any time in any market.

You don't necessity need to have a pre-existing substantive relationship.  

In case you didn't see the recent story about Airbnb regulations and limitations from the City of Louisville... https://www.wdrb.com/in-depth/proposed--foot-rule-aims-to-limit-airbnb-homes-in/article_26a7b458-5c74-11e9-a24f-272568002667.html

Flippers only want to flip to make quick cash, find a buy and hold investor [look to existing landlords versus flippers].

A heavy tax burden, regulations that push out businesses, and a power-hungry group of totalitarian sociopaths have been slowly eroding the city.