I can't answer honestly, because I have no prized childhood possessions. I'm not sure what that feels like. I moved to a different country when I left my fathers home and, aside from books, took nothing with me. I also have a habit of giving shit away I don't use anymore.
As for the prostitution aspect, I would go with no. Prostitution's legal here in Holland and it once came up that I didn't think I'd ever meet an attractive pre-op transwoman. One of my friends told me there were several decent-looking ones in the trans-hooker street (this is in Amsterdam, btw) and that she would be fine with waiting in the pub for me. I realized, as I'd never really considered the option before, that I wasn't personally okay with going to a prostitute, legal or not.
TL;DR: no.