I think it's more generally the phenomenon Paul Graham talks about: stuff used to be valuable and people didn't have much of it; these days, it's actually not of value and most people have too much of it. That is: we're all rich now, and we don't know how to cope with the fact.
It's moving up to a better class of problem. Like how Britain has a major health problem in 2011 with poor people being too fat, whereas in 1950 food was rationed. It's a great problem to have. Though it's still a problem.
Yes, it really helps to get in an outside view - the friend to help and berate you - until you get the proper visceral loathing of stuff.
I think this explains a lot of it. Another part is that people don't think about the costs of owning stuff: it occupies your space, you have to keep it organized, and you have to move it around whenever you move.
These costs are easy to ignore, because they aren't in mind when you're thinking about buying a specific thing. The mentally-available facts are "what will I get by using this?" versus "how much money does this cost?" Similarly, when you're looking for stuff to get rid of, it's hard to bring those costs back into light, because ...
I am beginning to suspect that it is surprisingly common for intelligent, competent adults to somehow make it through the world for a few decades while missing some ordinary skill, like mailing a physical letter, folding a fitted sheet, depositing a check, or reading a bus schedule. Since these tasks are often presented atomically - or, worse, embedded implicitly into other instructions - and it is often possible to get around the need for them, this ignorance is not self-correcting. One can Google "how to deposit a check" and similar phrases, but the sorts of instructions that crop up are often misleading, rely on entangled and potentially similarly-deficient knowledge to be understandable, or are not so much instructions as they are tips and tricks and warnings for people who already know the basic procedure. Asking other people is more effective because they can respond to requests for clarification (and physically pointing at stuff is useful too), but embarrassing, since lacking these skills as an adult is stigmatized. (They are rarely even considered skills by people who have had them for a while.)
This seems like a bad situation. And - if I am correct and gaps like these are common - then it is something of a collective action problem to handle gap-filling without undue social drama. Supposedly, we're good at collective action problems, us rationalists, right? So I propose a thread for the purpose here, with the stipulation that all replies to gap announcements are to be constructive attempts at conveying the relevant procedural knowledge. No asking "how did you manage to be X years old without knowing that?" - if the gap-haver wishes to volunteer the information, that is fine, but asking is to be considered poor form.
(And yes, I have one. It's this: how in the world do people go about the supposedly atomic action of investing in the stock market? Here I am, sitting at my computer, and suppose I want a share of Apple - there isn't a button that says "Buy Our Stock" on their website. There goes my one idea. Where do I go and what do I do there?)