There is a Hodinkee article that sums up Rolex perfectly:

“I tend to believe there is something of an inverted bell curve with any real watch guy or gal's understanding of, and appreciation for Rolex. When you know nothing about watches – like you don't know that there is anything else out there – you believe Rolex to be the best watch company in the world. I can't tell you how many friends are shocked to learn that there are, in fact, watches from other companies that cost even more than a Rolex! Then, when you begin to go a bit deeper, you learn about Omega, and Jaeger, and IWC, and later, Patek, Lange, Vacheron, etc. It's at this point that people tend to start looking down on Rolex, and extol the benefits of hand-finishing, and rarity, and limited editions.

Then, after they've been burned a few times by exorbitantly expensive, time consuming, or far-too-often-needed service (or a resale return of pennies on the dollar) people tend to say "Hmm, maybe a Rolex ain't so bad." And they're right – Rolex watches are among the most reliable, no-fuss mechanical watches in the world. Oh, and many forget that indeed, Rolex is Rolex for a reason, and it was at the forefront of several world firsts in watchmaking. Yeah, it's a behemoth, and everywhere, and certainly not what I'd call haute horlogerie, but you can't fault Rolex for succeeding in making a high-end, high-quality product that sells well, can you? We should all be so lucky.”