Yes, I wouldn't try a threesome.
Remove the boat maybe after removing the motor,sit the boat on the ground, repair the trailer, winch the boat back on the trailer, start bottom paint with the trailer supporting a portion of the load at a time then repower.
All of this can be done with an inexpensive motor hoist.
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'75 Cuddy with '00 Johnson Ocean Pro 150 horse
Benny
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