[quote=stumy;1657765] The OP is asking for sub-$1000 watches, so your suggestion that the OP "keep [his or her] choices" to the "harder to find" rolexes is not terribly helpful for this discussion. However, I find it hard to believe that the "run of the mill" Rolex watches do not hold "much" value. I believe a 1960's submariner will continue to appreciate...forever, and that value will be significant. Moreover, I was under the impression that any Rolex watch will retain a significant portion of its value.
There has been a surge in auction prices for rare vintage Rolexes. But that was probably driven by asset-bubble wealth and the desire among certain high-flyers to wear a conversation piece on their wrists.
Some of the more outrageous prices on stuff like Paul Newman Daytonas, James Bond submariners and Double Red Sea Dwellers probably won't be matched for a while, so if you bought a rare vintage Rolex at some kind of auction in 2006-2007, it may be difficult to recoup the loss.
In general, the secondary market for submariners is pretty good. The watch hasn't changed significantly in a long time, so unlike a lot of other brands, the watch from 15 years ago is pretty much the same as the one in the jeweler's case. In a lot of cases, the depreciation of the watch based on its year of manufacture (which can be identified from the serial number) is less than the inflation in the used market that results from a price hikes on new watches.
The Submariners, GMTs, Daytonas and Sea Dwellers seem to hold their value well because they are very iconic watches. The Milgauss is a new watch that has been sought after because it is scarce. Not sure how Yachtmasters and Explorer IIs are on the secondary market.
I know DateJusts hold their value poorly, as do Air Kings and ladies' models.
However, I disagree that Omegas shouldn't be kept. If you purchase a used (vintage) omega, I see no reason to think you won't be able to sell it for equal or more money in a few years. Seamasters, for example, will continue to go up in value as they become more rare. I consider old omegas the watch equivalent to the 73-89 porsche 911 models. They are great performers, and when you want to sell them, you suffer no depreciation.
Omega took a big hit to their brand value in the 70's, but they've been building it back up with marketing and endorsements. That said, they make too many varieties of watch, and they look too different from year to year. There's no consistent design like the Submariner, and that means that the watch is less of an icon and less sought after.
On the other hand, rolex is criticized for its pervasiveness. There are a lot of submariners out there.