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I agree with the "buy what you like and forget about investment" viewpoint. The truth is that no one knows what the future values will be like. In the end, everything is only worth what others are willing to pay for it.
As another poster said, values of collectibles are often highly correlated to one's generation. As an example, I have a baseball card collection from my pre-teens that I thought I'd sell for a fortune one day. I recently looked into what they're worth, and they're worth about the same as they were in the '80s, and that doesn't take into account inflation! Younger generations just aren't that interested in them.
Another example is cars, which are also items that you can enjoy and that can increase in value. Pre-WW2 cars used to be worth a lot more, but then the guys who really like them (those who remembered them from their childhoods) passed on. Same for '60s muscle cars. Watch Barrett-Jackson auctions and see who's buying those cars -- all Q-tips.
IMO, if you want an investment, go with a traditional investment vehicle, like stocks, bonds, and real estate. If the watches you buy increase in value, great. Just don't count on them to do so for your retirement.
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