I have never tried this in a boat but have done so in a car and it was rather difficult and I had access from under the car which you won't have on the boat.
I would recommend to pull the engine to ensure the old gasket and sealant can be fully removed to provide a clean surface so the new gasket will seal.
Dropping the pan in place will not allow you to pull it out as the oil pump pick up will prevent the pan from being slide out unless you jack the engine up. Then installing the gasket upside down will be a challange.
Can it be done; probably but the cost saving vs. what you will have to go thru are not worth it IMHO.
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1997 Silverton 362, 7.4 Crusaders
1997 2400 SCR, 5.7 Vortec / Bravo 2
Mike
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