Depending upon the slope of the ramp I let about 2 feet of winch strap out and re-lock the winch before backing down a ramp. When I reach the desired launch point I stop a little abruptly so that the boat slides back using that two feet of slack. This will break any adhesion to the trailer and get the boat into deeper water enabling it to float off the trailer more easily.
Also, if a straight back ramp approach is not available, when possible, the preferred approach to backing a trailer is backing the trailer to the left. Your visibility in the mirror and out the drivers side window is better than when the trailer is to the right.
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