I have zeroed in on a few markets (geographically and type of renter I want to cater to).

We went from zero to over fifty rental properties in about 10 years.

These are primarily found in cities with a population >1M.Pro-business environment: Many cities treat employers as adversaries through restrictive policies.

Generally speaking solid insurance and a good umbrella policy will provide ample financial protection for most liabilities.

@Jamie BanksI understand there are multiple parties: 1) displaced insurance policy holder (tenants)  2) ALE 3) The company that supplies all the furniture and install the washer and dryer. 

I had later found out, he had done ZERO work at all himself except for the times I was there and literally called him in and I had asked him to help his friend who was clearly struggling.

Third: even if your new toy qualifies for a huge depreciation deduction, your allowable deduction may be limited, and may even be zero.

Separate the work into 3 separate categories: 1) Those that are specifically related to the future STR usage, 2) Those that benefit you while living in the house and have zero bearing on the future STR, 3) those that benefit both you and the future STR....assign a percentage to the usage.Be specific and complete.

Though USLI, one of the biggest umbrella policy providers, dropped my max coverage to $1M because I had pools.

Regardless of which state you choose, be sure to maximize your liability on your renters policy and get an umbrella - this will protect you more than any LLC will.