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Notes -
In addition to the things other people have said, collecting also comes with the thrill of the hunt: if something is rare or poorly-distributed, it becomes a challenge to acquire them, which in terms of personal satisfaction can make collecting cheap tat somewhat fulfilling. You end up developing a knowledge of store distribution and release waves, which appeals to the spreadsheet-sexual among us and is actually kind of exciting if you're into whatever you're collecting. I'm guessing that collectibles brands that do rarity and distribution tricks do much better because they generate that excitement and FOMO.
With older items, it's a lot harder to have that same thrill because eBay has destroyed price arbitrage between insiders and outsiders. Anything valuable gets sold online; there are rarely deals for actually-rare collectibles.
But also, people just like stuff so when it's possible to buy more of it they often will. Believe it or not, grandmas actually treasured their Precious Moments figurines and I aspire to that level of simplicity of heart.
Thinking about elderly people's collections in particular, though: I think it's hard for younger people to understand the environment they lived in for much of their life. In their youthful days, the United States was more agrarian and less urbanized, and they certainly didn't have the immediate access either to facsimiles of the world's greatest works of art or to an algorithmized collection of curated aesthetic delights that we do today. They also lived before the advent of the interstate highway or the wide availability of air travel. For someone in such a less-connected world, the wide availability of mass-market kitsch served as an accessible way to add aesthetic appeal to their world. I get why people hate kitsch. But it's easy to sneer at things like Precious Moments figurines when I can type four words into Google and look at an image of the Trevi fountain. It's much harder when you live in 1940s Kansas.
I guess that's a reason I have trouble relating. My grandma is in her mid 90's, grew up more remote than Kansas with a father killed while she was a teen. She keeps an immaculate uncluttered house with no collectables to speak of.
I think your grandma is the exception. Most of the folks I know around that age are precisely like the people whose estate sale you attended.
My grandma-in-law's house is filled with shit whose retail value is less than the diminished utility they provide her through additional surface areas for dust. The upper floor of her beautiful house isn't inhabitable because nobody has vacuumed in years. But nobody in the family has the backbone to throw it all out.
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That's why I think it's better to collect stuff where the hard to find stuff is just harder to find and not necessarily more valuable. Consider record collecting. If you're looking for that super-rare Beatles UK first pressing then yeah, you're going to pay an arm and a leg for it, because The Beatles are one of the most popular bands in history and there are a lot of fans vying for the collectibles. On the other hand, if you're trying to collect the complete discography of an independent record company, most of the stuff you're going to have trouble tracking down is the stuff that didn't sell well and accordingly doesn't have a lot of demand; it's the kind of stuff that record stores price at a buck when it comes in (usually as part of a large auction lot) so it isn't sitting on the shelves for a decade. I love Bruce Cockburn and I buy original Canadian pressings of his records when I can find them (though the American ones are of higher quality) but I think the most I've paid for an album is like $7.00. This is the kind of guy who's incredible but little known; a bought a few of his records at a well-known used record store in Pittsburgh and the owner got excited and told me he intentionally marked the records down in the hope that someone would become a fan based on price alone.
On the other hand, while E-Bay has complicated the market a bit, it really hasn't changed that much. While E-Bay has made it more likely for someone who doesn't know what they have to get top dollar for a collectible because they happened to list it at the right time, you can still find deals the old-fashioned way if you have the patience. Most of the old garage sale finds are still garage sale finds unless you're talking about baseball cards or Star Wars toys or Christmas Tree ornaments or any of the other items that seem to only exist as collectibles. If someone has a painting they're under the impression their mother bought at a starving artist's expo in 1966 they aren't going to go to the hassle of listing it individually on E-Bay on the off chance that it's worth something. If you're eagle-eyed and happen to discover that it's actually a Whistler, then you've made the score. In the pre-Ebay days, most of the stuff that anyone thought of having any value was either sold through dealers or through listings in specialized collector's magazines. I'd estimate that the number of people selling genuinely valuable stuff at flea markets, garage sales, and the like isn't that much lower than it was in the '90s.
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