I have moved my Hobie 16 on and off the trailer by my self, and it was rather tiring to do it, plus it was going on grass on such. Another option is after you get the boat on the trailer, you could check into one of the trailer dollies for moving the trailer on land with out the vehical. i know that they can move boats with reletive ease on level ground, and are rated for about 3 thousand pounds. The ones I have seen also have a handle on them for easier moving
They do range in price, i believe that they cost about $150.00.
The Skier