@Jaydubya: FWIW, in my experience, divers will only replace yoke tank o-rings when they fail at the dive site where little attention is paid to carefully cleaning the o-ring and the o-ring groove. When they do replace them, they use one of those pre-packaged save-a-dive kits which comes with crappy Buna-N duro 70 o-rings. There's no telling how old those o-rings are or what kind of conditions in which they have been stored.
Good point regarding the failure of yoke o-rings on rental tanks. I agree that, from the frame of reference of the diver renting yoke-configured tanks, those o-rings seem to extrude more often than the o-ring installed on a DIN reg.
To be fair, though, just because an o-ring is stressed twice as often does not necessarily guarantee a 200% failure rate.
I'm not an expert on o-ring manufacturing, but I'd like to think that a scuba o-ring in a static application can withstand several hundred (thousands?) relaxation-compression cycles.
I'm not an expert on o-rings either but I do have some related experience. I wasn't really thinking of the relaxation/compression cycles since my intuition is that both types of o-rings ought to be able to withstand many load cycles. I was thinking more of the possibility of them getting damaged by a bur or a piece of debris as the regulator or whip is attached to the tank.
I think your idea of regs being cared for better than tanks also has some merit. Being stored in a dirty environment could be a source of debris. Being stored in a higher ozone environment for instance could also accelerate material breakdown. Most elastomers that I am aware of breakdown faster in an ozone rich environment.