Being the cultured anime nerd I am I know some things about this, though most of what I know on this comes from the anime nerds from across the pacific.
The reason for the fascination with high school is that in Japanese society, that tends to be the last time that people feel any sense of free will, and that post-HS life is a series of societal railroads where trying to jump the rails just leads to failure. So a lot of people end up idolizing their high school years. This is especially so among the main consumer base of anime/manga/VN/anime games, who are often the people who tried to jump the rails or just never bothered. They idolize their high school years to a fanatic sense, and the industry capitalizes heavily on that. There's a reason they can easily sell Madoka figurines or blu-ray sets for the equivalent hundreds of dollars.
This is an oversimplification (yet it's how that paragraph reads), but is it like the whole country felt like they peaked in high school? Like my jock friends that are now 30 and still display their trophies from a dozen years ago?
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