I am from MA as well, and Terraformer is a friend. He and his Comm2A team have done a HUGE amount of work on behalf of gun owners here.
Daugherty16... MA is may issue, but it really ends up being at the discretion of the chief of police of your home town. The town I live in has a very reasonable COP and licensing policies. When my daughter turned 21 she applied for and received an LTC-A with no restrictions (license to carry class A, the best license offered). Yet a friend who lives in Boston, who at one time taught firearms usage and safety for Brinks and still is an NRA authorized firearms instructor, has a restricted license and cannot carry. Go figure.
The policies vary widely from town to town, but in general the further you live from Boston the more likely you are to get a LTC-A.