I don't know anything about your setup, but I remove the user accessible O-rings from my Nikonos V and flash after every trip and replace them with "storage o-rings". In my case, these are old rings I've marked with permanent ink. This replacement includes lens rings, the loading door ring, battery compartment ring. The flash cord and extension tube rings. are not under compression, so I replace them after a thorough cleaning.
O-rings do get flat over time, but most camera rings can be removed, cleaned and lubricated without damage to the ring or seat. There are obviously o-rings and other "gaskets" that cannot be removed without damage. These need to be left alone.
The credit card trick is the best for not damaging the ring or seat in cases where simply sliding your fingers around the ring from opposite directions is insufficient.
Examine the ring carefully (under a loop, if possible) for any scratches, dents, cuts or deposits. Check and see the ring out of round. If you have any doubts, replace it.
Remember not to overlube the ring. Use a compatible lubricant and wipe away any residue. You should have as shiny ring with no globs or specks of lube on it.
Finally, double check your seats to make sure are clean.
Do this BEFORE and AFTER every trip or day of use.