I will add an item to this list and believe it should be near the top of the list: what are the current STR regulation and what is the sentiment.  

@MIke Steuart I haven't done a lot in Mass. but my understanding is that if you have an investment property, and it's not owner-occupied, then if you pull a permit whoever pulls it must have the CSL (construction supervisor license).So if it's your investment property, and you don't live there but you want to do the work (or supervise others you hire to do the work) then yes you'd need a CSL to pull that permit - or hire someone who does have it.I haven't done an apples to apples comparison, but my understanding is that generally CA and HI are Democratic places with lots of rules and regulations - like Massachusetts.

We have been managing short term rentals in and around Bozeman since before they enacted regulations on them, and have close to 1,000 5 star reviews.

I see from your response some of the issues I was expecting to be the biggest barriers to entry: capital and regulations/time to get approvals.

The main challenge has been dealing with the state and other governing bodies in regards to the water well and sewer treatment plant.

The main challenge has been dealing with the state and other governing bodies in regards to the water well and sewer treatment plant.

You also need to survey the local regulations on short-term rentals if some were going to go that way and see if the area is for or against them, in general.

There are three main categories to consider:Confirm identityDo they pay their billsWill they maintain the propertyConfirming identity includes a government-issued ID with picture and knowing how to spot fakes.

I've consulted with attorneys who suggested that the City is violating private property rights and the Constitution for forcing people to enter into a rental contract with the government, so there may be state and national implications.Was wondering if anyone else here was pressured into accepting Section 8 vouchers from current tenants and if so, what the outcome was. 

@Gerardo Waisbaum To be honest, with all the new regulations around documentation for cost segregation that has come out, I recommend having a professional do them.