I think there other factors more important than how many dives. In fact, the more often you dive, the better off your o-rings are, IMO. What you don't want, is for o-rings to dry out. With that in mind, how you store them between dives is most critical. The way the o-ring is used on the housing is another factor to consider. Ikelite for instance, says their house is designed so that grease isn't necessary for sealing. With my Ike house, I have replaced the main o-ring only 3 or 4 times over a period of over 3 years and about 450 dives. I inspect it EVERY dive. If there is any kind of flaw in it, it will be replaced. If it will not be used for a couple of days or more.I rinse it in lukewarm water, blot it dry, grease it lightly, and put it in a baggie. Most important is to not stretch it or use it dirty. I have had the Ike DS125 strobe for 2 years and about 300 dives and replace the o-ring when I replace the battery pack. Once so far.
The buttons need to be soaked in and worked in fresh water as often as possible. They should be cleaned and lightly greased when they get sticky - but on the INSIDE only. Greasing them on the outside will only collect sand and create problems.
I just got an Ocean Images Video housing and they told me to keep 2 o-rings. One to use to store the camera, while the working one is kept in a baggie waiting for use. This sounded like excellent advice to me. Especially if you don't dive often.
Probably the VERY MOST IMPORTANT thing you can do regarding o-rings, is to inspect them EVERY TIME you close the housing. With your glasses on if you need them! If there is the slightest bit of sand, grit or hair anywhere near it, clean it off. Create a routine and don't vary from it. You also want to inspect it as soon as it's in the water. If it's transparent, it's easier but if it's not, look for bubbles coming from where they shouldn't. Everyone knows that 99% of floods are operator error. That means they can be avoided if you don't get complacent.
I'm no engineer - this is only my opinion...