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IIRC watches, unlike some other similar assets, don't attract CGT. A bit like wine. So there's that.
Personally my biggest worry would be market liquidity. If you're retiring in 10yrs I think you can be reasonably confident that you could easily sell a day-date or no-date sub for money. In 30-40yrs? Probably, but who knows?
If you have an edge in a particular esoteric investment, then it makes sense to exploit it, as you stand a chance of better multiples than one which you have no edge and is full of other punters. My bet is that 9/10 the people with good knowledge probably made a decent % on day one by buying under market value.
hugo7
It's possible as part of retirement planning. Presuming you have other types of investment it might make sense to keep what is essentially cash to hedge against currency devaluation in the form of watches. They are easy to store and move around and there's an active market for them and people are willing to pay cash for them. Similar to gold in a sense but you can actually store it at home or wear it on your wrist without people asking you odd questions.
I doubt many actually go up in value over the course of a lifetime to make them a better bet than shares, but perhaps it's reasonably simple to pick ones that retain their value quite well and might go up if you are lucky. In a bind you could then quickly sell them to release cash or pass them on.
Unless you were very lucky they won't make you rich.To do that you'd need to pick the watch/es that everyone wants in thirty years time. Go!