Keep in mind that not everyone is familiar with the area so they may not know anything about the school districts, nearby public transportation, or nearby amenities.And if your property is the one I'm thinking it is, I think it could probably use some cosmetic upgrading like Michael mentioned.Just my two cents.

Besides being so close to transportation, the house is 3 blocks from Main Street in the village, which is about to begin a huge revitalization program.

(I used to own one in MA).They rent mailboxes and receive packages and also have a real street address, like "123 Main St, #456, Boston MA 01234"This also solves the problem of shippers who won't ship to PO boxes.I think there are a few Postal Center USA locations near you.  

It's a matter of geographic access due to transportation at the time, human behavior and statistical probability, not politics...

Yeah you could ground lease to someone else without owning the parking lot business.Older parking lot's in town can be valuable as Uber and other ride type share services are getting people around without themselves having transportation.

Hi Jaysen,Thank you, they seem to be doing it everywhere @ Boston area wasn't sure what all was involved. 

(*Direct Quote from an Attorney at one of Boston's biggest law firms.) ... and from them?  

I recall so many people telling me in the early 2000s, don't buy a place in Boston, you are too young, you want to travel etc.

You need a car with lots of trunk space to transport your open house signs,folding chairs and small folding table (for vacant properties),snacks and drinks,etc.

Some deals okay but Portland is Boston now it’s awful.