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.

There are many brokers who are geniuses and blow me away.The problem you have is; you have to read to re-read all the above to cover what I need to say.Your biggest hurdle is whether or not you can do some simple math, but the math is not simple in the sense that it takes a few minutes.

With one account and one credit card, all revenue and expenses are automatically imported and it takes about a minute or two, each day, to assign them to the right property.

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). 

Find a realtor who owns several revenue properties, not just one who has sold a few.

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

Your broker may be your biggest obstacle to wholesaling.