The biggest danger is hidden structural damage.

I've explored the cost and the requirements both personally and professionally as a site and land use civil, and the biggest savings is in reduced construction time.

Now I haven't been in the STR game for long, but I do happen to have the largest portfolio of long term rentals in the Cleveland market so take this for what it's worth.....Some speculation based on some semi related experiences being the biggest name in the game in regards to LTR's.To me a lot of the problems you are encountering are a direct result of what type of property you're renting out.

One of the biggest questions is - what is your long term goal? 

Hi Becky, In my opinion the biggest differences for landlording in MA and NH are taxes and regulations.

Although I attribute my kids to why I bought rental so maybe if I didn’t have kids I wouldn’t have rental idk.I am getting ready to start my first out of state deal and I think the biggest think for me is the contractor.

Never look for properties through a broker or on the internet that is listed for sale on an MLS service, zillow, or any other website.

The town that have the biggest problems with them, from what I've seen, are stemming from two main things (again this is my opinion, no data to support it). 

U should be talking to your managing broker about this not the internet LOL..  

Hot market was definitely the biggest challenge for us, but forced us to learn about REI.