It's interesting as recently I have been selling all of my modern Vintage Collection / Retro / Black Series items off, with the thought that the "solid" collectible/investible (and personally for me the most nostalgically connective) items to hold on to are the vintage Kenner items. Perhaps the reality for the more recent generations is that something like a VC64 Revenge logo Slave Leia is more coveted than a 31-A Back Hoth Stormtrooper?
That is entirely possible. Nostalgia evolves in our minds through the memory of what a toy is connected to, not through the toy itself. There are toys we play with for a while, and then set aside, never to think about them any more (and sometimes your parents dig them out and swoon about how cute you were playing with this and that, but that's their memory and their emotion and not yours, and you just shake your head and go on with your life because that toy is
done). And there are toys you remember later on, and you stop by the toy store window to look at its newest incarnation and imagine how you felt as a kid and how happy you would have been to own this new stuff - but still, you don't go and buy it again, because other interests have taken over your mind, maybe you used to build with Lego and now you build a garage so things may be still connected but you don't need that toy any more.
And then there are the toys that stay with you because they are anchored in the most powerful memories. You remember sitting with your father in the theater, and there were heroes on the silver screen and knights with lightsabers and spaceships, and it was double awesome because your mom only ever took you to Disney animations. And the next day he went shopping with you and bought you an X-Wing and a Luke, and you still know how it smelled strongly like plastic when you ripped open the bubble. You played with your dad (when he was around and not watching footy) and your brother although your brother was little and didn't see the movie yet but you told him everything and he got to be a Jawa. And all was well with the world, in a way it would never be again. You would return to that happy place when the real world was awful, and since it was in your mind, it would never ever go away, and those figures are the forever anchor that help you remember.
A kid today might make similar memories, but they don't get a Vintage Kenner figure; their anchor would be whatever is in stores, which may very well be a TVC figure. Or perhaps (sadly) they may not experience any attachment to a movie because the movies were only on TV and the advertising industry successfully managed to chop up any film into ad-compatible bites and there is very little excitement left with those ruins of movies. So the kid switched to computer games for their immersive experience and Super Mario or Fortnite will be their fond forever place.
When you talk to your parents, and they happen to still have a toy of their own, they will have those memories connected to it, but for you, it is entirely meaningless. That tin train, that box car, that autographed photo of Errol Flynn don't mean anything to you. You can't even imagine that this stuff is worth anything (and most likely it isn't, not anymore, not these days), and once you inherit it, unless an ancient collector offers you a sum, it will end up at the thrift store, at the flea market, or on the trash heap. Those memories are gone, those happy places are dead, and what remains has no intrinsic value and offers no nostalgia to you.
Same will happen to Star Wars stuff sooner or later. Since there is still new content being produced, there will always be some new fans, but for younger people the Kenner figures already have only abstract meaning as predecessors of what
they grew up with. And many new fans will not be interested in those specific toys (at least not to the point where they would spend huge sums on them) because they started a collection with Episode I or with Clone Wars toys. Some may buy Kenner Vintage as investment seeing that the prices went up for so long, but it's a fragile bubble. Every once in a while, an older person may enter the market because they rediscover Star Wars for themselves, but that is not an inexhaustible reservoir of customers.
And sure, there are now Retro figures to quench the nostalgia for many. It's just not the same situation as in 1977, so if someone really wants to "invest" through Kenner Vintage, they better guess right when the prices are maxed out.
