[chumbucket]

A set of good solid blocks will do. When it comes time to put it on the trailer, you'll want a set on each of the most aft and outer points possible (on the two rear corners under the transom). Then a third set under the keel at a point just ahead of the middle of the boat. Of course the boat, when on these blocks must be just higher than the rollers of the trailer. Line up the trailer in front of the keel blocks from the front and nice a parallel until the rear most cross member of the trailer just contacts the keel blocks. Then, with a hydraulic bottle jack just a bit ahead of that rear most crossmember, jack the front of the boat until it is up off the first set of keel blocks. The place those keel blocks in front of that cross member and lower the boat onto them. Remover the jack, and back the trailer to the next crossmember and repeat the process until the trailer is at least 2/3 of the way under the boat. You shouldn't even have used the winch up to this point. Once the trailer is far enough under the boat, lower the boat onto the trailer rollers. You can go ahead and clip the winch onto the bow eye, then using the winch, the trailer will be pulled under the boat to the rear blocks. Jack up under the keel in back, and remove the blocks. The boat can then be winched the remaining distance to the winch post.
There you have it. it's really not that difficult and should only take 30 minutes or so. Good luck with it.