This is something I've gone through many times. I have a small collection of 20 watches, and I've found myself wanting, or thinking, of downsizing it to a manageable 5 pieces. Each time though, I could never just get down to just 5 that I liked, especially since every piece has been studied, tried on, hunted, saved for - all of them have their own significance and milestone. It was painful enough just trying to build a rationale with regard to what stays and what goes, that I eventually gave up and made peace with myself with the fact that all of them get worn and that all of them have a significance in my collection. I've set that upper limit to 20 though and I suppose that for now, it will stay at what it is, and unless there is one that has to make way, no new pieces will be added. Vintage....now that's a new topic, a new box and a totally different argument....but I'm not there yet 