Nothing wrong with Rolex--it is just a decent middle-of-the-road watch. Due to successful marketing they have transformed their image into a "luxury brand" when the truth is that they make a decent watch but nothing special at their price point. Most of their movements are outsourced so you are actually buying the caliber of movement found in a $2k or so watch and paying the Rolex markup. In addition, the neavou riche and the Jersey Shore crowd tend to gravitate towards the brand as they see it as a status symbol--further cheapening the brand.
These and other is why watch affectionados stay away. I do like some of their vintage stuff but I would not wear one for fear of being associated with that crowd.