It sounds like the trailer was worth the $250 by itself. When I was looking for a used Hobie 16 (20 years ago) I found that they were holding their value and I ended up with a new one instead ($4300 with trailer). I never regretted it. I know the price of a new one has gone up where it is prohibitive. Sailboards seemed to cut into the Hobie market for a while (when Hobies got too expensive) and the quantity of 16s around eventually brought the used price down. Keep your eyes open as you ride around and you will be surprised where you find them. Look for the best condition boat you can afford or as said in the above post you end up working when you want to be sailing.

Howard