Keep in mind that rental market fluctuates so you can't always assume that rental income with increase year-over-year.Agree that it's becoming increasingly difficult to find value in towns near Boston, but if you continue to search there are nuggets that show up.

I grew up in an SEC football town and toyed with the idea of doing an STR there before, but it ultimately made more sense to go with a true, mature, vacation rental market.

The whole northeast part of town doesn’t have a lot of promise of improving.

Yes, Granite Falls used to have an issue with Meth but, to say that our town has a HUGE meth problem is seriously exaggerating.

If so, what area of town? 

I'm not suggesting a terrible area of town, but a less expensive area for a house that is outdated, dirty, needs paint, carpet, appliances, and new flooring.

Good to hear Bryan (although you won't find prices like that here other than in the absolute worst parts of town) 

Add a spare bedroom for out of town company and we are at 6 bedrooms.

I bought a $120k house to flip in my LLC name on the best street in town.

The buyer on this deal came from a town I do very little marketing or networking in.