I would never ever buy a new Rolex. Maybe a really old one, an antique, but not a new one. To cite the famous actor Nicolas Cage from the master piece movie Gone in 60 Seconds: "I saw three of the at McDonalds yesterday. And that tells me that there are too many people with too much money and not enough taste in this town". Rolex, to me, is like a golden Bentley, only their to show even the poorest dude that you are rich. Money doesn't buy taste or style so. Some Rolex are nice, most seem to be bought by people only to show of wealth.
Not to judge so, because there are certainly enthusiasts out there that own the Rolex of there dreams.