Does your friend have a NY pistol permit?
If he does, then the handguns (part of father's estate) can be added to his permit (permit amendment - all it takes is some time and some cash). If he does not have a permit, things can get (more) confusing.
On the Mass end, the executor of the estate would have to comply with Mass law, whatever it is. If noone has a valid Mass FOID for the guns, thenit may very well take a LEO to transport them to a dealer.
A few years back, my father passed, and I got some of his handguns. He lived in NY, and I don't. My brother, who also had Dad's guns on his pistol permit, had to take them to a dealer who shipped them to my home state dealer. I was in NY at the time, but I could not legally transport (or even touch) the handguns, as I did not have a valid NY permit for those guns. And the dealer could only accept them from a valid permit holder.
Cost me $80 shipping and insurance (the NY dealer "gave me a break") for three handguns, but it took a month, because the NY dealer would not accept the copy of the out of state dealer's FFL that I had with me. He would only accept one that came direct fromt the FFL, and that added a week or more. Oh, well, I did finally get them free from the tangle of laws that is some northeastern states.
Good luck.
