I don’t know, Friends did the same for pre-9/11 20somethings and I don’t mind watching rewatching the early seasons of that. And look how many memes there are from friends. I think there’s more to it then just the cringe factor of looking back.
My working theory is that puzzle box shows like HIMYM and Lost don’t hold up on rewatching because you get invested in the mystery (who’s the mother - what’s going on with this island) and now you know so the shows kind of lost.