Not Ranked
I've been watching this entire thread and have tried to put myself in the OP's shoes. Given the investment plus the emotional value in putting together one's dream car, and add in the fact of limited driving and, for the most part, driving sane enough not to attract too much attention, I'd personally be more apt to finding a way. What I mean by that is breaking the local laws (to a point). At the end of the day, what could be the absolute worst thing that could happen? I would think a car impound and a trip to the judge to get it back (plus a hefty bonus to said constable).
To enjoy one's freedoms, sometimes you have take calculated risks. A VT plate or whatever is far better than just sitting on one's hands figuring out what to do (or not). Meanwhile, keep searching for the vintage block and once you have one together (and barely running), get it re-registered in MA, pull it out and replace with the real one. Sure it's a total hassle, and it won't be cheap, but you could also be dead tomorrow. Drive the freakin' car and enjoy life (while you still can).
My $0.02.
-Dean
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