Welcome to NES to all of the FNG's. It's always good to see new members because it means that the number of people interested in firearms, and our rights to own, them are growing. Just applying for and getting an LTC shows that you are serious about preserving what many people in the rest of the country take for granted.
I hope that this will not discourage you. You should also know that even in the best of times, there is a strange phenomenon in Mass that I call "Gun shop Grumpy". It's been talked about on the forum many times. I am not sure why it exists, but it probably has something to do with lots of tire kickers and that some gun owners like to window shop as a form of entertainment.
There are a few things you can do. First is try to narrow down what you are looking for before you look to buy. Go to the rental places and see what you like and then keep your eyes open for it. You get a lot better results if you call a shop and say " I am looking for a 1911. Do have any in stock?" As opposed to, "Hey I am new to guns, can I spend an hour finger f***ing your inventory and then leave because I don't like the way anything feels in my hand?"
Don't be afraid to buy a quality used gun. If properly cared for, a decent firearm will last forever. Most people will never shoot out a barrel. If you do, buy another one. The classified here are a good place to look.
Rim fire and even quality air rifles and pistols are a good way to get shooting for short money. Sig now makes quality stuff that are great for training and the triggers and action are very realistic, with the added benefit that you can shoot in your back yard.
Welcome aboard new folks. Don't get discouraged. Shoot often and shoot safe.