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with or without gear oil in the drive? The drive should be empty.
While pressure checking you can do a couple of additional test while under pressure.
Twist the shift shaft, spin the prop by hand, twist the ujoint assembly and see if you can create the leak, you have to listen very carefully.
Water intrusion typically comes from the shift shaft seal, prop seal (s) prop carrier oring (rare) water pump base seals, upper gear case seal that seals the gear that drives the vertical drive shaft. Also and the most common location is the two screws (vent) and (fill) the oring/fiber gasket is missing or bad.......use a pic and clean out area where gasket goes and use a new on on both locations...