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i can't advise about Mass taxes..
but if you are not keeping the boat in the water than don't paint, like sokinwet said.
If you are going to, then make sure you barrier coat. I agree you will save much money, get the saitfaction of doing it yourself, and MOST IMPORTANTLY, you know it was done right. It is such a PIA process (not difficult, just tedious) that I bet a lot of paid painters skimp/cheat/don't pay attention to detail.
There has been a ton written about the topic, and the interlux website has great info. It is basically a FULL day job, but thats it. Prep the boat in the AM, and then start painting. The thing with the epoxy barrier coat is that you have to start the next coat while the previous is still tacky. You do 4 coats like that, then throw on two coats of ablative, in alternate colors if you want a wear indicator.
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