Minimizing Taxes; Hailing Port
If you want the freedom to use the boat in Mass, even for a few weeks a summer,
PAY THE USE TAX.
MA harbormasters diligently check marinas and mooring areas for permits and registrations. The moment the state learns you are a resident with a boat in the state, you will PAY THE USE TAX, plus penalties and interest (which doubles the tax due in 3-4 years). The DOR staff collecting use taxes have no senses of humor, and you are guilty unless you can absolutely prove you haven''t kept the boat in state...
If you can afford a boat you can aford to pay the taxes to enjoy it in peace...
(When living in MN in 1994 I finally paid the use tax on a R19 I had purchased in ME in 1990 while a MA resident. MA discovered the sale after I had moved out of state, and was all but eady to send a Statie out to MN get me for thier $400. Since I expected to move back some day, I finally settled when MS dropped the penalties).
IMHO, PAY THE USE TAX.