That's awfully expensive, but if he takes care of all the paperwork, it may be worth it... especially if there were any liens on the boat against the previous owner. I believe that the USCG charges a bit more than $100, but don't remember the exact amount.
If you're going to be sailing in foreign waters, and Canada does count as foreign waters nowadays, being documented is generally better than be state registered. Also, in some states, like Massachusetts, there is no need to register the boat with the state if it is USCG documented, so if you're keeping the boat a longer period of time, it can be cheaper to document it. Finally, some financing for boats are actually marine mortgages, and as such have better financing terms, but generally require the boat be documented.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.