I have bought and sold far too many watches. My love of watches has been constant, but somehow I went from wanting one, 24x7 watch, to owning several. It started with a Rolex GMT II Coke bezel. Then I traded up to the Two Tone Blue sub. Literally wore both watches around the clock. Now, many, many years alter, I often wish I could just find the one watch again.
That being said, if you find one really expensive watch you feel could be the "be all, end all" it might be worth the chance of trading away all that you have for one. Perhaps put an end to the constant craving of the next watch. What is that old saying about not getting what you want, but wanting what you have?
For me, it never worked out that way, when I had the very expensive watch, I often missed those gems that I had found great deals on. Maybe that one watch is still just around the corner, but for now it's not..