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1. On Saturday, launch the boat and tie into slip.
2. Take the trailer home, sand and paint.
3. Go back to the boat and out for a sail.
4. Anchor out overnight, and sail all day Sunday.
5. Come back to the slip in the afternoon.
6. Go fetch the trailer and haul out the boat.
Just launching the boat reduces risk of having an accident that damages the boat or hurts you.
You can block up the boat and pull the trailer out from under, but you'll spend a lot of time doing that, that you could spend sailing.
But if you insist doing it at home,
1. Jack up one side of the trailer and block the boat.
2. Lower the trailer.
3. Repeat 1 and 2 on the other side.
4. Now with the boat elevated off the trailer, start pulling the trailer out from under.
If you have a trailer cross member that comes against your blocks, just block immediately behind the member, remove the blocks immediately before the member, and proceed.
Good Luck Ramblin'
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