Conclusion:
Today I will lube myself up good and nice, bend over for daddy government and do as I'm told, like a subservient little subject.
While I've moved to PA, I unfortunately still live so close to NY that I frequently travel into and out of the state for various reasons on a weekly, if not daily basis. I'm fortunate that I live in what might be the only PA county which has a deal between sheriffs that reciprocity can be granted if I go through all of NYs application hurdles. As others have pointed out, one of the questions on their application is that I've never had a license revoked.
By now I've probably got a small handful of enemies at both the MA local police department, as well as the MA firearms records bureau. If they're not counting down the days to revoke my license, at the very least, they've got a paper trail that I've provided them which doesn't comply with their interpretation of the "law". So, it feels a bit like I can choose this hill to die on, and find myself pretty significantly restricted from carrying around my home, per NY state's "laws", or I can just comply.
So there it is, fellas! You've witnessed the results of coordinated state overreach in effect. If anybody elese finds themselves in a similar situation, I'd recommend that they consider either not notifying anybody in MA at all, or attempting the "drop off the license at the police department on your way out" trick.
The whole thing is absolutely absurd. I hate that I'm doing this.