And it's not only homes, it's all the infrastructure a city needs.On the insurance issue, I think this may be the end of national carriers.

Each week, I analyze the MLS, exploring cities and towns across South Florida to identify areas favorable (or not) to short-term rentals.

Any city or area anyone has had success in recently?

I have a client in Kansas City that does this.

It seems Safeguard is genuinely trying to clean up the Jackson, MS, mess but they are also marketing lots of other deals in other cities still.

The City of Detroit is block-by-block in many Class B & C areas.In our opinion, zip codes cover too large an area.We use Detroit Neighborhoods, which are much smaller than zip codes.

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.

Every Week I scan the MLS, navigating cities and towns in South Florida that are friendly (and not friendly) toward short term rentals.

What if they build just outside the city limits, so they are not paying city taxes?     

Once you know how the land is allowed to be used by City or County zoning, start working to a "highest and best use" mindset where you find out how the deal can be quickly turned into money by the end user.