Airwaves !! I can answer your question first hand! We just went through this last spring.
Towing a trailer with NH tags behind a vehicle with MA tags does not make you a target for a traffic stop -- no more than if you borrowed a neighors utility trailer (provided it is duely plated & registered) and tow it.
Our new boat is Registered in NH -- much to my chagrin, as I had a Mass "vanity" boat registration that I wanted to maintain (single digit with my initials). We still register the trailer in MA - this was done for consideration (ambiguity) in the language of our Umbrella policy. As Merrymeeting said -- talk to your agent!!
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