What if your tastes change and you decide to sell one watch to buy another? Even if you smartly bought on the secondary market, the value could still have gone up or down (as you note), and of course vintage watches can only be bought on the secondary market. Should you still be unconcerned at that point?
I will deal with that when the time comes, as I have done. Again I'm not a flipper, so I don't change watches a lot like some do, and I tend to keep what I buy, even if it's something I don't wear much. I'm not under any pressure to sell anything, so if I only wear it a couple of times per year, that's fine it can sit in the watch box. Again I expect to lose money when I sell the watches I have, and I expect this hobby to cost me some money over time. I don't know if jhross98 is a dealer or not, but I'm not, so I don't look at buying and selling watches as my business - I earn my living servicing them, but the watches I buy are my hobby not an investment.
The watches I have sold I have lost money one, there's no doubt of that, but I wasn't concerned about them. Not because I am super rich as jhross98 has incorrectly concluded, but because I've enjoyed them while I've had them, and I'm happy to let them go to someone else to enjoy. The annualized cost of owning them for the time I did wasn't outsized compared to the enjoyment I received. I've said this in other threads but a friend of mine looks at purchases for watches (of which he has a far nicer collection than I do) or pretty much any other hobby as "enjoyment units per dollar" and if you get enough enjoyment units for your dollar, and can afford it, then where's the problem?
If you look at jhross98's purchase of his own Journe, he broke his own rules, buying it when he says it was performing worse than ALS on the secondary market. It is now become the market vanquishing master that he loves so much, but if he followed his own investing rules he wouldn't have that market monster now.
My view is that if you are going to limit the watches you collect to "sure bets" for gaining value (if there is such a thing) is that you will be forced to buying a rather narrow choice of brands and specific models, and you would miss out on some truly fantastic watches.
Hope this explains where I'm coming from. Again if others want to look at watches like the stock market, that's fine it's their money. But looking at every watch as an investment would not make this hobby any fun for me. it seems this type of collector (really an investor) has become very common these days, which is why all the talk on many forums is about flipping stainless steel Rolex sport models that in the past I could typically walk in and buy without having to pay double the list price - to me that is far more insane than buying a watch I like but will probably lose some money on down the road if I decide to sell it. The market has spoken, and I'm not interested in what it has to say for the most part.
Cheers, Al