Getting a MA permit isn't that difficult (it's easier than for residents), but the $100 per year is "off-putting." You need it -- I don't. I'll take the chance that I am unlikely to be attacked by zombie hordes while transiting the MA Turnpike en route to Maine.
It's very sad that the birthplace of the American Revolution and the Minutemen has sunk so low with respect to observance of the 2nd Amendment. MA is one of the very few original states whose state constitution does not treat the RKBA as an individual right. Their constitution provides for the bearing of arms only for the defense of the commonwealth.