The cops have a lot of power over licensure in MA. In addition to reports of cops to the RMV, any police chief can have a license suspended at any time if they believe that the person presents a threat. This was highlighted last year with a spat of elderly drivers causing serious accidents. It’s problematic because their is no set standard from community to community.
In terms of what you can do, I would definitely get a CGM and develop a thorough plan for driving to present to your doctor. State exactly when and how often you will test and how you will respond to a low. Then talk to your doctor. I’m sure that they will do it if they can document that you are ready to get on the road.
I personally have not encountered this in MA because there is no specific regulation for diabetics. I do not declare it as a medical condition that will affect my driving.