I don't get sentimental about bikes or skis. I currently have 3 bikes - road, commuter & MTB. Wife currently has 4 - road, grocery bike, MTB & trainer (it was cheaper to get an old bike and an old trainer than to get an exercise bike for her). I've sold several bikes over the past few years during my quest to get the fleet I now have and am happy with.
That doesn't mean I wouldn't buy several more if I had the money and space. I'm sure I could "justify" several more styles of bikes (at least to myself, not so sure about convincing my wife).
As for skis, there was a time when I had a good pair and an old pair for when conditions were bad and I knew I be gouging the bottoms on rocks. Now I just have one pair and don't ski when conditions are such that rocks would be an issue.