Actually in MA it is due to the vehicle having more than 5 wheels... It is considered commercial private not for hire... If you use it to make $$$ then the state police can pull you over and then you need a medical certificate because the vehicle is over 10,000#. You do not need a class B lic. in MA to drive the vehicle. The only way that they will hassel you is if your hauling and especially for profit. It cost me $238.00 to register the truck and $750 for insurance in MA. It must be registered yearly. I did a bunch of research on this and talked to the registry and the state police truck enforcement division. Also, if your truck is prior to 1985 you do not have to worry about fuel exhaust, but do need to have a safety inspection yearly...
I suggest getting familar with the place your going to have the truck inspected as it will take an hour just because they want to really view the truck more so for conversation.
Like some of you said. I take my truck out weekly and have never had any issues. I wanted to drive it when I wanted and I went the commercial route for plates... I use the truck with my son's scout troop that I help out with too and it has come in very handy with 30 boys in the troop.
We drove over 3,000 miles last year and I never thought we would go more than a 1,000. Most law enforcement will not bother you as long as your not traveling over the speed limit... Try doing that in a duece. You more so need to worry about the fools that are pasing you and cutting you off.
Good luck!
Northeast MA