Big collecting mistake/regret?

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Not buying a PP Aquanaut ref. 5167A-001 with papers for $21K back in June 2018. The dealer told me "it's better than owning gold, and the value will only go up." Current price: around $100K on Chrono24. He also had a Nautilus ref. 5711 with papers for $46K (current price around $175K), so arguably not buying that one was the bigger mistake in terms of value, but I find the Aquanaut more attractive and the price was more realistically within my budget at the time. I still have my notes with these prices in the Simplenote app on my phone.
 
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Interesting, seems the grass is always greener. I regret being way too conservative and financially cautious in my early years when the watches I liked were much more affordable. I deliberately passed up many amazing opportunities.

Now it’s too late to spend anyhow as the prices are simply unrealistic for my taste, in many if not most instances.

Funny to see from your comments there may be a silver lining, and maybe I also avoided many mistakes at the same time.
 
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Not being patient and not having acquired enough knowledge to properly evaluate a vintage watch. That was particularly true when I started collecting and resulted in my buying several watches then with polished cases, dial damage, etc. that I wouldn’t buy now. I lost money on virtually all of those early purchases when I later realized my mistakes and sold the watches.
I can relate to this. I think the more you get into it, the more you realise you don't know. I guess it's a process
 
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I don't regret any watch I've bought or sold. I enjoyed them all for what they were, and some I learned lessons from (I am actually not a fan of two tone for example).

The only regrets I have are for watches I failed to buy when the opportunity presented itself.
 
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I find my mistakes are balanced out by my successes, but that's purely from a collection value point of view. I don't buy anything with a view to make money, but I prefer not to waste it.

I have bought many watches that require work, that's my issue. I never get around to getting them fixed. I have more projects than wearable watches. I have changed bezels, crystals and bracelets, but you soon learn that anything more than that should only be done by a professional.

I have six speedmasters, but only 2 that don't require work 🤦

It has however been a fun journey, and that's what it's all about 😀
 
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... are you less happy because you own more watches ... or because of other reasons and more watches can not cure this? 😉
Even 10 years ago I didn't look in watch dealer windows, search ebay (except for bicycles), or read watch websites. Now that takes up in increasing portion of my time looking at things I like but cannot afford.
 
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😟.. as Crosby, Stills, Nash & Young were singing... " if you cant be with the one you love, love the one you with"... if you know what I mean 😉😉
Edited:
 
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My biggest regret is not buying the Rolex Sub Kermit when it was readily available.
 
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Not going all out on this one grail watch that came by on eBay
 
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Not buying a PP Aquanaut ref. 5167A-001 with papers for $21K back in June 2018.

About that same time, I glanced around at RO Jumbos and felt the prices were crazy at ~$25K

 
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Three Daytonas I bought in 1988 for $2,000 each, flipping them for $4,000 each, and thinking, “How can you complain after doubling your money?”
 
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Reading your comments, I realize that thanks to you and OF, I've kind of avoided too many mistakes regarding conditions and originality as I just had 2 watches when I came here. So most of my watches are actually very nice (more than half of them coming from here) and I can't individually regret them. Thanks for that !👍

BUT I do realize now only 4 years after having got myself in this hobby that I've let some very nice watches pass thinking they were out of my league... realizing now that I've actually spent several time those amounts on what could be considered as 'too many' different watches...

So some kind of cleaning is due if I would really want to raise up my game 😀 But I've told this to myself a year ago and I keep not putting this in practice 🙄
 
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I definitely regret some purchases I didn’t make but equally I regret some sales.

I’ve found I can be too hasty to release a watch from my collection if on a whim I decide it’s too small, not my current taste etc.
When I get that feeling now I try to remember to put the watch away for a while and try it again after a bit of a break. I do this several times before I finally decide to sell.
 
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Not trusting my instincts to buy key vintage pieces I immediately liked - when they were affordable!

Buying 3x watch winders which I never turn on.

Otherwise, I’ve enjoyed the journey, new friends made and shifts… now knowing more what I like, it’s time to shrink my collection.
 
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My advice to new collectors is to take it slow. I have a little bit of regret at the speed in which my collection grew once the vintage bug hit me. I think I missed some opportunities. OF course I’ve also not yet learned to let go.