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Do what makes you happiest and have no regrets either way. The watch you leave for your grandson in the future will have more sentimental value of you wore it regularly and signs of wear are present. To directly answer your question, I have sold / trades 4 Omega watches over the years. The first generation Planet Ocean 45.5mm, the 2220.80 (one of the watches that Daniel Craig wore in Casino Royale, but obviously not the screen worn piece), a vintage Seamaster from the 60s, and a 2225.80 which is the chronograph version of the aforementioned Casino Royale piece.
The first Planet Ocean was sold to fund a. Explorer II back in 2010, zero regrets. Have I missed the watch at times? Not so much, and if I still had it I would likely sell it anyway.
The 2220.80 was sold and the cash used for other things at the time because I had the 16570 Explorer II at this point and wore nothing else. Do I miss it? Not really, as my collection has been rebuilt better than before in the present as I type this post.
The vintage Seamaster, 2225.80 (which I've replaced by the way and will never sell again), and even the 16570 Explorer II were all trades towards a 116710LN GMT Master II at a bricks and mortar business in Toronto. Given what has happened to the watch market, I'm SO glad I did this back in 2017 when it was much easier to do or obtain. Do I miss any of those watches? Nope, only the one that I ended up replacing, of course.
As aforementioned, I have since added many more pieces to the collection in the past few years and couldn't be happier! Life is short, live it to the fullest do always do what makes you happiest. Hopefully this helps but either way I know you'll be happy as this is yet another win-win situation.
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