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In general you'll find that several bits of info for changing out a cutlass without pulling the shaft. Its doable but it takes the right tools.

Doing it in the water adds a whole other level of difficulty and potential problems to it.

First you have to find a diver that is willing to do it and has the tools and knowledge to go with the willingness. That guy is probably going to cost you at least $100 an hour, probably more. In San Diego a diver charges $150 to take off a MaxProp and $150 to put it back on. I know cutlass bearings and MaxProps aren't exactly apples to apples (but your prop will have to comeo ffto change out the bearing) but its something that takes willingness, knowledge, and the right tools. Not every diver has all three.

Might end up being best to leave it for a haulout. But for sure call up the dive services in your area and see what they have to say.
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