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If you read the old thread I re-posted you will see that I was also hesitant to drill the holes and raise the motor. It probably took an hour total time the first time.
On the second boat it was probably 15 minutes. By myself both times, although I did use a Bobcat with a cable to the hoist ring built on the motor the second time. Used a thick epoxy fairing compound for the old holes, but as others have said a dowel soaked with resin would be fine.
I predict when you do it you will be amazed and your only regret will be not doing it sooner.