Yep, Rolex certainly has the desirability factor, while Omega does give you more options, not just in size, but also in configuration. Going through the various options on their website will take you some time, because there's just a flavour for everyone.
The watch that we dream for is definitely a Rolex, though Omegas and Grand Seikos are the ones that we can get today - relatively affordable, and no waiting lists... :-)
RE: Omega Speedmaster Triple date.