Just keeping one watch from your collection...

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Easy. I'd gift all except one to the kids in the knowledge they won't wear any of them. Then I "borrow" them back for care & maintenance purposes. This approach avoids the need to make any tough decisions.
Are you a lawyer by profession?
 
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less stress to just ask what's your favorite watch
 
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To keep it really simple, if it was for financial reasons like OP said I would probably keep my quartz Seiko 7A28. Lowest resale value in the bunch by far.
 
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If creating cash is the real objective, then I would sell everything except a G-shock.

The most practical keeper would be my Rolex Explorer, but it wouldn't be the most exciting one.

Given my Avatar, it makes sense I would try to keep the Lange Moonphase.
It's stunning and the pictures don't do it justice.

 
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Silly collectors... forgetting it's not the watches, but the hunt to find them that makes this game so compelling.

If I had to though, I find this simple diver a nearly perfect everyday watch. "Nearly" only because the date window breaks the symmetry.
 
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that polerouter is really nice man. I wouldn't be able to sell any watch from that collection man.
The Polerouters are the bomb lol! Still don’t know why they don’t get as much respect as the Rolex’s of that same time period... the design and quality are amazing!
 
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Are you a lawyer by profession?
Ha, what made you say that, was it the statement about avoiding the need to make tough decisions or just, in general, my cunning plan? In fact, I'm not a lawyer. Alas, if I was I'd most likely have more watches to gift the kids. But I'd also insist they sign some document ensuring I have continued use, just in case. Disclaimer: Apologies in advance if I've offended any lawyers here. 😀
 
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If I can only choose one...

Before the craze and for a big life milestone. This watch of mine started my obsession almost a decade ago.



pic from crown caliber.
 
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So assuming this is a financial decision, I would sell all of them. Then I would go back to where I started, and re-buy a Hamilton Khaki Mechanical:
 
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Ha, what made you say that, was it the statement about avoiding the need to make tough decisions or just, in general, my cunning plan? In fact, I'm not a lawyer. Alas, if I was I'd most likely have more watches to gift the kids. But I'd also insist they sign some document ensuring I have continued use, just in case. Disclaimer: Apologies in advance if I've offended any lawyers here. 😀
You've said it all. 👍
 
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Ha, what made you say that, was it the statement about avoiding the need to make tough decisions or just, in general, my cunning plan? In fact, I'm not a lawyer. Alas, if I was I'd most likely have more watches to gift the kids. But I'd also insist they sign some document ensuring I have continued use, just in case. Disclaimer: Apologies in advance if I've offended any lawyers here. 😀

are you a linguist?
 
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This question comes up a couple of times a year. I'm pretty sure my answer is different each time.

This time I'm going to have to go with the modern ploprof. I'm moving tomorrow and I need a good water proof watch.

 
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If selling due to financial stress then I would sell them all.

Once the concern had gone away I would start again. Cool watches don’t have to break the bank.