I have been a watch addict for five, six years now but it only took me a short while to realize that:
1. One cannot possibly own EVERY piece one likes. There will always be the next Basel/SIHH...and no matter what you have, there will always be a more attractive proposition.
2. One should clearly understand why a particular piece appeals and not care too much about what other people says about the watch
3. Having said that, one's tastes may change (this is the most horrible moment), so one has to be pretty sure that a new acquisition will last... one way to achieve that is to refrain from making impulsive purchases and if one cannot loose a piece from his/her mind for a whole week, then perhaps that's a keeper.
4. If you can afford it, go for the best - compromising will only lead to regret
As for me, I am very happy with what I have (compared to a few years ago) and I consider myself lucky to be able to develop the current portfolio.
Best
Sam