It's hard decision, I don't collect games. But unless I'm forced to, I won't part with the PS1 game disks I have (they don't work anymore). Because I feel if I disposed of them I'm disposing of part of my childhood.
I still do dispose of things I care about... I think the same of anime/manga/programs/games downloaded/installed on my PC, I need to dispose of them periodically because I can't afford to buy new HDD for all the anime/games I have downloaded. It's a hard decision to choose what to keep everytime but these days I'm more likely to do so than to keep my PC full.
Have a nice day with daughter/family, I'm sure she's cute.
When (if) I have family of my own I'll probably be willing to dispose of my past keepsakes for them!!