A good rule of thumb: for black o-rings use Nikonos grease. For colored o-rings, use Sea & Sea grease.
The function of the grease is to keep the silicon o-ring supple: it is not the sealant! In fact, be careful to NOT use too much because it will attract that fearsome destroyer of o-rings: sand. As far as how often to use it on non-photographic equipment: usually I grease flashlight o-rings just before a dive trip and just after. The rational is that just before gives me the chance to evaluate the status of the o-ring and just after gives me a chance to clean off any salt water or detritus.
Of course, if you change lights or batteries, you need to remove the ring evaluate it and regrease it or replace it.
For photo equipment, I do also check the o-ring just before a dive trip. However, during the trip, I do not fiddle with lens or lens port o-rings unless I have changed the lens or the port. By doing that I reduce the chance of damaging the ring. For film door seals on u/w cameras such as the Nikonos, I check the o-ring each time I open the door; and I regrease it. For the camera "door" of a housing, I do the same. That is because the act of opening either may allow a piece of sand, etc. to interfer with the seal. By regreasing it, I can evaluate the groove for the o-ring and the o-ring itself.
One more time, I need to emphasize that LIGHT GREASING is the word: the grease just keeps the o-ring from becoming dry or brittle. It is not the sealant.
Scorpionfish--that's not an old o-ring: that's my upper lip!