[Puddin'_Tain]

A diver should be able to do it. However, if you feel comfortable doing the job yourself, it may be cheaper (or pretty close to a wash) just to haul the boat, change the cutlass yourself (and inspect the rest of the boat's underwater bits), and launch the next day to avoid lay days.

 

[Puddin'_Tain]

Now that I think about it for a minute, I suppose it depends on whether your boat has a fin keel and the cutlass is in a separate strut, or your boat has a full keel and the cutlass is inside the trailing edge of the keel. In the case of the latter it might be way too difficult for a diver to get the old bearing out. But, in the case of the former a competent diver should be able to do the job (assuming that the shaft is fairly well aligned). Although, as I said above, it might cost less just to haul the boat and do the job on the hard (and hauling the boat gives you a chance to look over all the underwater bits too).