I'm slowly working on how to decide/qualify which watches I keep and which ones go... and I'm trying to be very strict about it. For me there are 7 levels of watch "affection", right now my rule is any watch falling outside of categories 1-4 are watches that need to go. I imagine the reasons for watches to sit in each categories will be very different for each person. For me I can tell you that $$ value plays absolutely no role, it's about the watch itself...:
1. Precious: This is the highest level of love. It is impossible to qualify a watch in this category in the beginning of ownership, because when you're in that honeymoon phase all watches feel a bit of this level of affection. This is the watch that if something were to happen to it, you would be devastated .. you would undertake all unreasonable measures to repair or replace...
2. Elite: Simply put, when you put this watch on you think to yourself... you know... I could be happy with just this watch.
3. Sentimental: This is a watch that holds sentimental value... you may or may not LOVE the watch itself at levels 1 or 2 above... but the sentimental value behind it means you'll never get rid of it. Watches given to me by my wife, or to mark a special occasion fall here. These watches often get little wrist time... but it's as important to simply own them as it is to wear them.
4. Fantastic watch: Everytime I put this level on.... I think... holy crap this is a nice watch, man why don't I wear it more often? If this watch were to be lost, stolen or sold... you'd be ok. But you'd certainly miss the watch, and speak highly of it to anyone who would ask or be interested.
5. Nice watch: Wow this watch is really nice for what I paid for it... or wow this is a really interesting piece when you consider the history.. or something along those lines. Usually this is the watch I'm thinking about selling, but contemplating keeping just because it's such a nice watch. Even if I don't LOVE it.
6. Bubble: These are watches really on the way out... I'm trying different straps, I'm asking for opinions, I'm checking the pre-owned market to see how many dollars it could yield.
7. Oops: These are watches that you know immediately aren't right. For me they get classified as a mistake and I try to offload them as fast as I can.
Watches in category 6-7 you have to be careful... just like the honeymoon phase for new watches... there's an immediate letdown right after the honeymoon for many watches. I feel like you really have to give the piece some time before you qualify it as a 6 or a 7.