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$5000 for a Rolex would net you a Rolex Explorer II (give or take a few hundred) probably.
If you head down to the states, Fox's Gem Shop in DT Seattle has a great selection. If you head further south, Tourneau is the place to go to.
Locally I bought from Palladio. Great after-sales service as well.
You should also be aware that once you buy these kinds of watches, you need to get them "cleaned" or serviced every couple of years to avoid the complications in the watch to deteriorate. These "cleaning services" normally cost a few hundred as well. Rolex routine cleaning can range from 2xx to 4xx based on experience. Same for Omega and Panerai.
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