When to upgrade?

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Suppose you've got a "good" Speedmaster and you're happy with it but, because you're an OF member, you keep looking anyway and a "very good" example of the same reference comes along. You have no desire or intention of having 2, unlike many OF members, so although you can afford the VG you would expect to sell the G. For the sake of argument, you are not a regular buyer/seller of watches, nor do you ever plan to have a 'noteworthy' collection. Your watches, one of each model you desire, are simply for your own enjoyment whether they appreciate in value or not.

How do each of you decide whether to upgrade to the VG or simply be content with the G? If it was VG versus Excellent, or G vs E, does that change your mental equation?
 
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The answer to that question is variable for each person. Some have no need to update a particular watch because a better copy comes along, others are always looking to get a better condition watch. I don't do much vintage any longer but I never felt the need to upgrade, each watch stood on its own..
 
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Worthy question...

and for me, it's always PIO (Pride In Ownership). If I did my due diligence, took my time with research (meaning options), vetted properly, etc... I stay satisfied with what I have purchased.

It's similar to marriage - always going to be a visually better looking option out there, especially when the years keep ticking by, but what's underneath the hood means something: the experiences, the moments, life with all of its glorious patina.
Or as Paul Newman once said about Women, The Movie Star Life and his marriage to Ms. Woodward: "Why would I want hamburger when I have steak at home?" ~paraphrased because I didn't go to Google to check*
 
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Depends how much enjoyment I get from the current watch. Often, there are specific aspects of a given watch that I really like, even if it might not be as valuable as a "better" example. However, TBH, I would usually take the opportunity to upgrade if I could do it at a fair price. If you ever do decide to sell, it's always easier to sell a better watch.
 
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I only have one and I am wearing the crap out of it! If one day I upgrade, I’ll wear the crap out of the next one too. It may go from E to G but it will still outlast me!
 
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Of course, the real secret is to buy a VG or E one initially. But now that you have the G one, I agree with others that it depends how you feel about it. If it’s condition is now bothering you and diminishing your enjoyment, trade up. If not, stand pat.
 
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If you're talking pre-moon, I'd say upgrade every time you find a nicer example than the one you own. If you're talking modern, there's no point upgrading.
 
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Better the devil you know……

But your asking people that would buy 7 of the same watch….😗
 
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Interesting question as I just did the opposite very recently. I had an excellent example but was not comfortable wearing it so I traded it away and bought a still a G to VG one that has seen some life at a lower price that I can enjoy wearing without any concerns.
 
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Interesting question as I just did the opposite very recently. I had an excellent example but was not comfortable wearing it so I traded it away and bought a still a G to VG one that has seen some life at a lower price that I can enjoy wearing without any concerns.

The proverbial "double edged sword". Many of us buy as nice as an example as we can find. As a result, they aren't worn for fear of banging them up.

Yeah, I'm in that boat.
 
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Always go from good to very good. Never go from good to excellent, it’s probably relumed, repolished……
 
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The proverbial "double edged sword". Many of us buy as nice as an example as we can find. As a result, they aren't worn for fear of banging them up.

That's why I prefer wearing modern watches. They are both nice and replaceable.
 
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Without intending to, I’ve seemingly established a pattern of upgrading and then selling the newer, better example. I guess I’m more attached to the first one I got and the better example is easier to find a buyer for.