What do you consider weird in Mass? Up until the past year the state set insurance rates and a lot of insurance companies chose not to do business in Mass. That changed last year and all the internet insurance companies are now doing business in Mass, it hasn't seemed to have helped or hurt.
In Mass you are assigned risk based on years of driving experience and driving record. I have never heard anyone having an issue with compulsory insurance because of the age of the car. The insurance companies unless you go to a Haggerty or the like won't give you agreed value on the collision or comprehensive but if you go to them you can't use it as a daily driver either.