there isn't supposed to be any caulking around the gimbal housing... It has a rubber seal... if it's leaking then the transom is probably rotten (Lets hope not)... the bellows should be replaced every few years... they are not fixable, just put new ones on
in order to seal under the rubrail you will need to remove it... not NEAR as hard as it sounds
use 3m 4200 or 5200.. silicone won't last
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