Massachusetts isn't as bad as some people think. . .IF. . .you happen to live in a town where the chief of police is pro gun. Some towns give them out left and right, others not a chance. I don't believe Massachusetts has reciprocity with NH, Maine, or VT so if you visit Boston plan on leaving your firearm at home.
That being said, just because MA isn't as bad as some people think don't get the idea that we are firearm friendly. If gun laws are a major factor for moving into the region then you probably don't want to come here.
I agree with Shafter's comments here. I've had a Massachusetts class A concealed carry license for some years - no problem getting or renewing it. I also have a non-resident NH license. As others have noted, Vermont requires no permit for concealed carry, so I can carry over much of northern New England without any legal hassles. Although I believe Massachusetts is a "shall issue" state, my sense is that there may be a fairly dramatic difference between the ways in which the permitting process is handled in western Mass. (where I live) as opposed to eastern Mass. and especially the Boston area which has a reputation as being particularly gun-hostile.