So funny you should recommend Rolex, because I actually know a few people who own them(and they all bought them brand new) and the prevailing opinion is that they are absolute crap at actually being a watch - they just drift a lot in short amount of time - one of my friends says his is can be as much as 10 minutes out every month(!!!!!) and that's a 5k watch!!!
I'm personally saving up for an Omega, you can get a timeless design for 2-3k, and those watches are truly indestructible and actually keep time accurately.