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If your's is a center board then It sounds to me that Mark is right on. If it is a fixed keel perhaps I can help. When I first got my boat a friend and I used to have it in the water & sailing in 40 min. When I do it now it takes me twice that time because I usually am doing it alone and don't do it very often anymore since I'm now on a mooring.
I'm building an aluminum gin pole similar to Ray Henry's. (Ray, I did build and use a wood one and your right it is to damn heavy) I also mark on the goal post with tape how far I need to put the trailer in. This is very important on the fixed keel since the trailer will be completely submerged. I'm sure a tongue extension would help although I don't have one. Liquid rollers is a big help.
Ed
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