I look at a driveshaft bellows like I look at tires, if I see small cracks starting to form it is time to replace, that is a sign that the rubber is becoming less flexible. Tilt the drive all the way up and look in between the folds, if you compare an old bellows with a new one you can see and feel how much stiffer the rubber gets over time. Also turn it side to side, see if you see any signs of abrasion as well. In my use (salt water, moored boat 6 months, but when stored drive is down) I start to see cracks after about 10 years of use.
If the gimble turns smoothly when turned with fingers, and you're not getting any noises from the drivetrain I see no need to replace it. Mine was last replaced about 20 years ago, never any water in the bellows since then, it gets greased at the beginning of each season with the engine running and that's it.