A very subjective question based on the person's financial positions and general usage/principles of a watch, but I've noticed that in my collection I have quite a few daily wearers, these are generally easy to maintain quartz watches to older swiss watches in the sub $3000 mark. I don't really think about selling them, and don't really think about the watch throughout the day.
However, there were a few watches I've owned that came to me in excellent condition (and they generally range $5000+ USD) where I start thinking:
"Maybe it's a bad idea to swim with it even if it says 200m"
"This might attract unwanted attention in a bad neighborhood"
"Might be bad to wear too often if I plan on selling it"
A funny moment I remember was when I was walking with my father, and my Rolex GMT II tapped his Breguet Tradition Seconde Rétrograde, and we both immediately grabbed our wrists as if we were in pain to check for any marks on our watches.
At this point, the cost of the watch is deterring me the enjoyment of it being worn often, and only taken out in specific occasions. I generally convince myself not to buy the these watches because of the lack of wear time and the high costs of service. Curious if others get the same feeling for watches in their collection, and if they also thought about 'that' watch that they start babying more than others?