Losing everyone you love? Well, that just makes me think of Air.. Yeah. One of the few animes I've seen where the ending isn't a happy dandy one.
But it's held in a fantasy world so cable cars wouldn't fit in that.. would it?
Another one, I think, might be Karin. The ending is a total twist though. XD
Peach Girl is definitely a dramatic story about losing the one you love. It's very very shoujo.
