Only to a watch geek.. I own 24 watches. One is a Rolex. Mine is a 1996 model. I have worn it for a long time.
Let us look at the facts:
1. A Rolex is hardly expensive when compared to other Swiss made watches. Sure a Rolex costs a lot more than any Chinese made, American or Japanese branded watch. But, compared to other Swiss brands a Rolex is nothing. A Gold Rolex Daytona with diamond markers is only about $50,000. That is "chump-change" when it comes to watches.
2. A Rolex will only be noticed by other watch collectors. It is a "nerd" item. No woman is likely to notice it You may as well have an iPhone 5 strapped to your wrist. .
3. The idea that a watch holds is value is utter foolishness. Buy a new laptop and keep it for a year. See how much you can get for it. For the most part, a watch is no different. Buy a new Rolex, then try to sell it at another dealer the same day. You will get less than half what you paid for it.
4. Most high end watches are mechanical. Mechanical watches are based on technology that has not changed much since the early 1900's. Most (Rolex included) only come with a one year guarantee. You must get the watch serviced every four years or so.
5. Rolex are often faked. A fake Rolex is worth less than nothing.
6. If you are not 40 a Rolex will not look right on you. Rolex is popular with young gay men, so if you are under 25 or so, you will be casting yourself in a stereotype.
7. Rolex is so well known because the name is easy to say. People who are "fake" will often buy a Rolex because it is the only brand known to them or the people who they are trying to impress.
8. Gold is a pretty lame material to make watches out of. It gets damaged easily. Stainless steel Rolex outsell gold Rolex by about 2:1.
You can go on Amazon and buy a nice Invicta for about $100. It looks similar to a Rolex. If you get tried of it, then give it to goodwill, and buy another model.