I currently have 2 watches, both popular Rolex models. The first is a hulk bought in 2018 from an AD. It is worn daily and not babied, worn in the gym, lots of scratches etc. Plan to keep forever.
I was able to mentally justify the purchase of the second watch because I knew it would hold its value if I hit hard times. It’s a BLRO and I’d imagine when I bought it from the Wad, it was worth almost double what I paid. I was never really fussed about resale value (above retail) but I think I would feel a bit disappointed if they start selling at say 80% of retail or below. Having said that, I’m fortunate enough not to be close to hard times (as far as I know) so the value is kind of irrelevant.
I don’t think members should be judged if resale was a consideration when they purchased the watch. I bet there are members here that ‘couldn’t care less’ about the value of their expensive watches, but still would only buy pre-owned cars because they want to avoid the deprecation you get from brand new.