I'd say my biggest problem with stuff is the aspirational things and the emotional things. The skinny jeans you hope to fit into again some day (I've gotten good at getting rid of those things lately though). The t-shirt that's now too small but was a thoughtful gift from my kid. Otherwise I'm pretty good at purging things, it's more a matter of having the time and energy to tackle such projects.
I do start to think of my kids now too when I'm purging and organizing, the whole "Swedish death cleaning" concept. Not that I'm anywhere near death - anticipating at least 30 more years! But after dealing with my mom's things after her death (which were few and well-organized - she purged most of her stuff when she moved in with me 10 years ago) I realize that my stuff needs to be better organized and accessible to my kids in case of my unexpected demise.
