I am a "keeper" myself (not quite up to hoarding status), and DH spent 22 years living out of footlockers and doesn't think anything should be kept, so it gets interesting at our house. Both kids are cluttermonsters as well.
I was only able to get rid of certain clothes (outgrown by DD6) last week by taking pictures of them for posterity -- most of it she was willing to put in the donations bag, but some were sticking points. I will note that the same strategy worked for me when I managed to allow myself to get rid of some toys that I had had since I was a toddler -- worn, ratty stuffed animals full of love
who went into the trash after having their pictures taken.
We keep boxes in the closet, one for each child, which are for the "save" papers and artwork, but most ordinary assignment papers get tossed. I tend to do that when they aren't looking, and they never ask. Sometimes DD will catch me tossing one that she wants to keep, but she doesn't fuss too much when I explain that all the special ones went in her box.
Toys, miscellaneous junk, all that stuff tends to build up alarmingly between cleanings.
