If any place has HOA/POA I would be very careful with those restrictions and talk to plenty of people including every board member before buying about their views on STR. 

Otherwise contract a service for the season that will automatically take care of for every snowfall.4) YES you need to heat them!

Be careful, these landlords are notorious for not paying 

A) there are those syndicators that have been at it for 5-10 years, made a killing in the COVID era run-up and maybe don't really care anymore.

I can give you dozens of examples of owners who believed they could care for their property better than a stranger.

I'm about ready to file a complaint on them with the FDIC.Moral of the story, it's a nifty application but I would be careful about how much money you keep in that account. 

Be careful on if you do, get multiple bids and vet the GC well. 

Reading those little books that guests and sign and comment in can be very helpful and grounding when you have those times when it seems like guests don't care.

welcome @Cam Caraher and congrats on joining BP, this place is the start for many, sure was for me longer ago than I care to admit.I'm not personally in your market, although was born in dorchester and grew up in NH, but this is a great place to meet locals.If you have not already a great starting point is the Meetups posted here, just search for your area and see if any meetups are happening. 

In my limited experience, HML may not care too much about your credit but they will care about your, presumed, lack of experience.