Damn, one hell of a company.
Ok...$10k to spend on a watch and with something left over so you can keep the stinger wet...let's see...
I'd go with one of the following for me, depending on my intended purpose:
- Omega Planet Ocean or Tudor Black Bay (Red, Black, or Blue) if I wanted a sporty watch I could wear everyday to work, in the pool, on vacation, etc.
- Omega Speedmaster Moonwatch if I wanted a sporty watch that wasn't a diver and has a great legacy/following
- Omega Aqua Terra for a nice in-between watch that will go from a suit during the week to shorts and flipflops on the weekend and look great doing both
- IWC Portuguese or Portifino if I wanted something more formal or to wear for occasions where I'd need to wear something other than shorts and flip flops
If you wanted to go for a Rolex, $10k will limit you to a few models due to 1) the retail prices, 2) demand keeping the cases empty, and 3) people who buy multiple watches from and AD getting things held for them. A couple of Rolexes that are great watches but aren't seeing the demand of the Submariners, Daytonas, or GMTs that can be had for <$10k and you will see at an AD would be the Explorer and Explorer II. It's not that they're bad watches, it's they haven't had any major updates in the last few years that's driving up demand like the others. If I were in your shoes and wanted a Rolex, I'd look for the Explorer II as it's a great watch with a GMT feature that you can wear to the office during the week, then go diving with on the weekends.