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With my old Grady 22 and my newer 18'CC I found the cost of getting it done at a marina made it the easy way to go. By the time you buy the paint, brushes, solvent, a little sandpaper, and tape, $10 a foot looks like a pretty good deal !
If you decide to jack it up, once you find the right spots to support it, you can jack the entire trailer up, place the stands or supports, and then drop the trailer back down. The big pain is the crossmembers of the trailer, you need to re support behind them as you ease the trailer foward. Some trailers are much easier than others to do this with. I have watched professional boat movers and they design or customize their trailers so that it is a real easy process. I found the easiest process was to bring it to the marina !
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