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I regret selling my old Rolex. I also regret selling my Nikons, Leicas, and lots of other stuff. If you need the cash to buy food or gas I can understand, but if it is just sitting there not hurting anything, I would say wait for a moment. Mayb it will make a good gift, maybe you can sell it to someone for a great price, who knows.
My first Rolex was sold and I have no idea where the cash went to, but I knew that watch. Even though I made money, I lost a memory. It would be like selling a pet.
If my Rolex leaves my arm before I die it will be because it was by court order or I gave it to someone. I will not even trade up, it will remain mine. I learned my lesson.
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