One other thing about NY, according to their state law (which I realize is in conflict with FOPA), it's illegal for an out of state resident to transport a gun through the state unless they hold a NY permit or are going to a competition.
http://www.nraila.org/statelawpdfs/NYSL.pdf
If he's coming back from MO to MA, he'll be driving through.
It also says this in parenthesise -
(A provision of federal law
provides a defense to state or local laws which would
prohibit the passage of persons with firearms in interstate
travel if the person is traveling from any place where he
may lawfully possess and transport a firearm to any other
place where he may lawfully possess and transport such
firearm and the firearm is unloaded and in the trunk. In
vehicles without a trunk, the unloaded firearm shall be in
a locked container other than the glove compartment or
console)