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I started to properly get into Digimon last year, like really following the chronological history. After all, I experienced Pokémon chronologically. Sometimes I wonder what it must be like for a kid who just starts with Pokémon, like do they see this massive backlog like most do with Digimon? At the very least Pokémon makes it easier to catalog and the only thing that really matters is the main series of games, which itself is easily split into Generations.
For Digimon, EVERYTHING matters. The virtual pets, the various video games, the various manga, the various anime and movies, the various card games, etc. They all introduce new stuff in nearly every iteration that comes out. You can't just quantify Digimon into evenly split Generations, you have to see them as eras.
The initial run (1997-2003)
Dead year (2004)
Savers resurgence (2005-2008)
Dead year (2009)
Xros Wars resurgence (2010 onward)
You can probably take most years and split them quarterly, like
>Winter 1998/1999: Pendulum v-pet, V-Tamer, Digimon World, WonderSwan game
>Spring 1999: Movie, Adventure TV anime
>Summer 1999: Card game, Digivice toy