What are you thinking about for a boat?  10.5 is the max I believe but it is a PIA to trailer a boat like that around these parts.    At that size you are probably looking at a trailer that is 35+' long.  The ramps and parking for gear that size sucks in MA.  Also, you will need a big truck with a towing cap of probably 12500+#.  Truck and trailer will be pushing 50'.  That is what mine is.  It is a white knuckle drill driving that rig over the CC bridge.  I usually drive down the middle  and let people blow their horns and flip me off.  That 15" granite curb looks like it could be a real problem if clipped.  I don't do it often any more. (thank god)
I cant say enough about the towing vehicle...don't under do it.  you could end up like this poor guy...
http://www.striped-bass.com/Stripert...ad.php?t=74576
(it snapped the hitch off and rolled over on the side of a highway as he was taking the boat home from the seller.)
My trailer reg is about 450 or so per year.  Considering I only put about 5 miles per year on it it is costly to keep around.
I would sell the trailer and let the yard haul/store it.