I have owned maybe 7 different Rolex watches and, while they are a great way to secure small loans, they may not be the be-all-end-all of watches or watch collecting. Having said that, it is pretty hard to imagine much of a watch collection that doesn't include at least one watch from this most famous company. I find the Tudor Prince Oyster to be the ideal example.
As you probably know, Rolex Watches are actually made using movements ordered from a "contract" manufacturer of movements, the ETA factory. Just as Rolex modifies many of those movements for their primary line (Rolex) they also use an ETA movement (as do many other watch companies) in their Tudor line. Tudor watches, though, generally use the Rolex Oyster case and crown, just like their more expensive siblings. What you are getting with a Tudor watch, then, is akin to what you get when you buy a Crown Victoria instead of a Lincoln. You get much of the substance without all of the prestige. For instance, whereas Rolex watches come in platinum, gold and stainless, Tudors come in stainless and stainless with a gold (or gold filled) "shell" on the top of the case.
With the advent of watch collecting in general and Rolex collecting in particular, a practice has grown up of "upgrading" watches beyond their factory specifications. Actually, higher end Rolexes have long been subject to customizing with jeweled bezels, special dial faces, etc. I suspect the first examples of this phenomenon among Tudor watches were done in an attempt to fool people, though the reasoning is not entirely faulty- after all, the crown and the oyster case (so called because it seals up tight as an oyster) are already there. What was not there when the watch left the factory was the Rolex name on the dial. And, in many cases, the dial was not the quirky and highly prized "California" dial, which has half roman numerals and half arabic ones. But, as the Doobie Brothers said, What once were vices now are habits. The marketplace has embraced this after-the-fact upgrading and now a new look predominates among used Tudor watches. They frequently have had the name Rolex added to the dial so that you no longer have to say "It's as GOOD as a Rolex" and, as mentioned above, they often have the snappy California dial. Informed consumers and collectors may approve or disapprove, but the practice seems to be here to stay.
Another helpful reviewer (Teleraw, a person I have not met or contacted in any way) has discussed the controversy surrounding this upgrading process in his own guide to the California Dials. I will not repeat what he said, but urge you to look for his guide and read it (and PLEASE vote "yes" for its helpfulness). What I am here to do is to tell you how nice these modestly priced watches are. And the answer is AWFULLY NICE. But the best part is not the redo of the dials or even the genuine Rolex waterproof case and winding stem. The best part, at least to my way of thinking, is the 34mm size. These watches are about the size of an American quarter (or a bottled water cap) and, thus will fit most wrists comfortably. This is not the Rolex that is big enough to use as a shield in a gunfight. This is not a Lady's watch, either. This is the midsize- large enough to read, and small enough to fit inside your shirt cuff. This is the Rolex for secure people.
In my experience, you can get a redialed Tudor Prince for about half the price of a similar Rolex Oyster perpetual. By all means, if you plan to wear the watch regularly, DO NOT BUY A MANUAL WIND ONE. Winding and resetting the watch via the screw down crown will drive you crazy- and likely strip the threads on the crown, if it hasn't already been done.
By the way, did you hear about the two Dobermans named Rolex and Timex? They were watch dogs.
As always, I recommend doing a little research before buying or selling any watch, especially one that will cost hundreds of dollars. Ask questions, read guides, watch prices for a while, then make your move to the watch that has style AND substance.