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Zac,
My brother has a roller trailer. He runs a line from the winch stand to one of the guide posts. When he returns, he gets onto the trailer like you, keeps it in gear, removes the line from the guide post and attaches it to the bow cleat.
Once cleated, he turns off the motor, hops out, attaches the winch strap and cranks it up.
He reverses the process when he launches.
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