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· Tartan 27' owner
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I changed my own cutless bearing on the hard a few years ago. Boy, what a PITA job that was on land. It took hours of labor. I can't imagine trying to do it in the water. Power tools don't work well under water!!!
I won't say that it can't be done in the water but you and I just can't afford to pay what it might cost to replace a $50 part.
Much, much, much easier to do on dry land without having to worry about the boat possibly sinking.
I wouldn't even ask a diver IF they would do it.
 
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