How do you know when it's a keeper?

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Only time will tell whether it's a keeper or not!
 
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The first look and whether the watch ‘speaks’ to me. will do some research and hold off a couple of days or weeks perhaps months. I would prefer having these ‘cooling off’ period and miss out some watches then having buyer’s remorse later.
 
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... the 2nd place is just another great watch I like but it's changing at least once a year.
By definition, if you are changing it once a year, it's not a keeper. 😉

"Keepers" either have (a) sentimental value, or (b) are iconic. The rest are disposable.
 
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Am not sure that there is such a thing as a "keeper", except in Association Football.
All watches are, IMHO, subject to whim and financial circumstance.
I would hate to sell my first proper watch, 76 Speedmaster, my grandfather's Lanco, my Carrera 2447S, the list goes on. But if it was that or no food on the table, they would all go.
I would also loathe to part with my much loved 1968 Autavias 2446. I bought this, as with all my watches, because at the time I really, really liked it. I still really, really like it.
When I bought the watch, many moons ago, the nickname "Rindt" was still waiting in the wings and these manual Autavias had minimal perceived value. Now with the explosion of vintage watch prices and cashed up collectors chasing the next "must have", I find myself with a favourite timepiece now considered valuable and sought after by many. Sadly, in these days of digital disruption and Covid, a long cherished chronograph is becoming painfully worth more to me as cash than a beautiful watch.
Hopefully the market will burst.....big time
Edited:
 
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My only rule on this issue is that I don't buy on impulse (as if I could afford to anyway). I only add a watch to my small collection if I could be happy with it as my only watch, if necessary.
 
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I wish I could claim as well that I don't buy on impulses, but as a matter of fact I do. Since I have a 12 watch rule (size of my box, limit not reached yet), there will eventually be some churn and turnover. I wish I could avoid it, as reselling comes with an effort, and I'm lazy.

So I was thinking of this thread in the middle of the night last night when my toddler son kept me wake and I've come up with my own scoring system from 0 to 10 (I know, not really innovative) for the subjective wearing pleasure, which can mean anything from pure aesthetics to sentimental value etc. The watch that I currently like the most and will beyond any doubt stay a keeper, a Seamaster that I bought here on OF, has a score of 9 and is the current benchmark. Anything below a 5 is a candidate to go.
I went further to create my own pleasure-to-price ratio to have a price-adjusted ranking by dividing the pleasure score by the purchase price in 1000 of my base currency. This ratio factors in the opportunity cost as I could have spent the money elsewhere. For instance, out of FOMO I bought a brand new Speedy Pro last Sunday that was offered to me 20% off the retail price (I thought I cannot do wrong with that. If I don't like it I can flip it without incurring a loss hopefully). The pleasure score is already lower than the mentioned Seamaster, I give it a 6 or 7. Divided by the costs, it becomes a borderline case. For now it's a keeper, but it depends on what else comes in or where my cravings go 😀.
 
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Apparently, all of my watches are "keepers" because I haven't sold one yet.

I wear some of them more often than the others.
.
 
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I've come up with my own scoring system from 0 to 10.
You are far from alone, and you would be amazed how complex some weighted-scoring systems can get. My own system has certainly helped me most at the extremes - i.e. >15/20 = so that's why I'm looking after that inexpensive watch so carefully; < 8/20 = what were you thinking?
I blame the ready availability of spreadsheets myself... 🤔
 
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I've come up with my own scoring system from 0 to 10.

I went further to create my own pleasure-to-price ratio to have a price-adjusted ranking by dividing the pleasure score by the purchase price in 1000 of my base currency. This ratio factors in the opportunity cost as I could have spent the money elsewhere.
You must be an engineer 😁
 
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When you feel like you need to wear it to sleep

Just don't do it with a radium watch 😉
 
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Every time I get a new watch, it has my attention until I get another lol. It's somewhat a honeymoon period. My so-called keeper from 2018 just left the box as I did not wear it as much. Nothing has been with me for quite as long but I have 2 watches from 2020 I believe are keepers: Rolex 1601 and Omega 14902 pie pan.
I literally hunted and longed for a DJ fluted bezel and an Omega pie pan. It wasn't an impulse buy of any sort. Once I got them, I felt so lucky. I think a keeper is something that you can toss on your wrist without any thought. And you never think of even selling it. You imagine you will pass them onto your kids or whatever. Basically, you take them to your grave.
Despite everything I've said though... we shall see if they beat my previous keeper (2 years) 😵‍💫
 
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They are all keepers, until they aren’t.

Couldn't say it better. 👍

The taste, the trend, the collecting strategy, the value : everything can change in time (even the wife !) so they are all keepers, until they aren't...
 
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To me, there is an element of scarcity to it. If I know that it will be unlikely to find a similar model in the future, then I keep it.
 
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You know it's a keeper when you keep it.

Unless you're a horder like me, in which case you never know.
 
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I'm interested to read what posters above use as criteria and the weighted scoring system to come up with the summary point tally they used to evaluate keeping a watch.
 
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You know it's a keeper when you keep it.

Unless you're a horder like me, in which case you never know.

What he said. And it's not always an instant bond, though have a "wow!" reaction the first time you see it in the metal is a good sign. Other pieces grow on you over time.

On a few occasions, I've made the initial decision to sell a piece in order to fund the purchase of a new one. But then I wore the first around for a bit and just couldn't bear to part with it.

Having flipped almost my entire collection three times over in the past decade (the only ones I've kept since the beginning are the Ranchero and a Connie 2852 I purchased back in 2016 from an OF member), I'd say almost every piece is now a "keeper" and I would have a hard time parting with them. Most of them (e.g. the Speedie, the HS9, the Nivada CASD) were "grails" and they have been immensely satisfying to own.

Then again, tastes change, and there's still a few "grails" out there, so you never know . . .
 
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I'm interested to read what posters above use as criteria and the weighted scoring system to come up with the summary point tally they used to evaluate keeping a watch.
It all depends on what's important to you personally. Horology, aesthetics, scarcity, heirloom potential, sentiment, money, all have their place in some schemes, But the blend can change as people and their lives change (hence the need for automated systems to tell us what our preferences are). 😉