As far as I'm concerned the less you play with your o-ring the better.
Every time you take it out to clean it you will stretch it a little and there will come a time when it becomes too long, doesn't seat right and you will get a kink and a leak.
On my housing that I first started started using in 2002, I lubricated well the o-ring and then for 7 years just rinsed the housing (closed) after use, let it dry, ran my finger very lightly around the o-ring feeling for any grit or salt which I would wipe off with a lint-free cloth if I found any, and then put a new film of lubricant. Even so, last month I had to replace the o-ring because it had "grown" to be larger than the seating.
Still that's 7 1/2 years regular use from the first o-ring with never a drop of water inside the housing.