I was hoping I could get some feedback on my reasoning, information about AirBnB/their unique rules, and recommendations on great real estate agents and AirBnB property managers in the area. 

A lot of investors shoot for $100/door minimum, so you've got a bit of cushion there.

After the first one, I'd advise to be more analytical than emotional, but do what you love, leave yourself some cash cushion, and jump!

The tenants will call a unique number.

@James YeeIt is the start of tax busy season so it will be hard to call an accountant now and ask them to answer a question unless you are already a client of theirs.The short answer is that you will be required to file a MA resident tax return(as you normally would do) plus potentially filing a NH non-resident tax return.NH is a unique state that it does not tax all types of income.

I have what feels like a unique situation and wanted to throw it out to the group to see if anyone has any thoughts.  

If they lose money on the flip, the 6%-9% paid by the homeowner will be their up-front cushion.

My first deal ever (which I was mainly hands-off on - the only reason I consider it a deal I was involved in is because my ex-business partner used half my money and half his money to buy the trailer) was a rent-to-own house trailer.It was a bit of a unique situation in that the guy who we had moved into the trailer worked for my dad and so we took his monthly payment out of his pay so we knew we'd get our money. 

Have you thought about selling the property -- makes it a headache to walk away from.The best thing to do is talk with a few local property managers -- long term tenants present unique challenges (State & local laws vary). 

I think it is great that areas are requiring PMs to have their own licensing as it is such a unique part of Real Estate.