Three key factors with watches exist for me:
1) The thrill of the chase is often more rewarding than the watch itself;
2) There are no scenarios where you truly “need” a watch, so you can afford to be patient; and,
3) You often don’t actually know if you like something until you’ve lived with it - and you generally end up liking things less than you think.
I probably bid or correspond on 200+ watches a year, either at auction or in classifieds. I maybe buy 3-5. Some I sell, some I keep. I don’t usually know if I’ll like them until I buy and live with them. I truly fail in love with fewer than I simply like, so I’m always trying to build leeway into the price to allow me to sell them if I don’t love them. Plus, I tend to have a few on hand to play with at all times, so it’s not as gutting to sell ones I’m on the fence about.
There’s also “drop everything grail pieces” that I’d want to sell certain pieces in order to buy - again, having leeway to do this and potential to at least break even in pieces helps build a collection.
For that reason, I’m very careful to maximize value. It’s a recognition more that I can mistake lust for love, rather than trying to profit off the watch. Plus it lets me try different brands, eras, styles, etc, helping me know where I want to go as a collector whilst minimizing downside.
Investment seems like a dirty word here - So maybe we can settle on the massively less sexy “prudent purchase, all things considered”.
