All depends how you look at it I suppose.
I offered to register the vehicle and they said they needed to and it wouldn't be a problem.
I even brought my registration form with the wet stamp (yes an actual stamp) from the insurance company but they still wanted to use their form (which the registry would of eventually rejected when it was submitted without the insurance stamp).
They didn't know the laws in MA, and it sounds like Aaron is taking action internally at MD to learn so i'm almost 100% sure my exact problem will not happen to someone else from MA.
At no point did I think MD was trying to screw me on purpose, they seemed to legitimately think they had over 30 days to register the vehicle and submit sales tax, and also think I was allowed to drive for the 45 days or whatever it was with a "temp tag"
Sometimes companies grow too big too fast and have growing pains, pretty common actually.