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Pokemon always brought this notion of men controlling nature and this mash up between the natural world and the virtual world. These monsters are captured by balls and turned into information. You store them in computers, trade them via cables or wifi, even fix them through a computer at the Pokecenter, no need for bandaids or anything. No wonder Pikachu stays out of it.
I believe the Pokedex works like a scanner that detects text, once you scan something and the text is computable, you can reproduce it and understand it, you can even burn the original paper. In the same way, when a Pokemon is caught for the first time ever, there are no information to the Pokedex and this Pokemon is not only "scanned" throughly, but captured, destroyed and rebuilt as information you can use. The fact that the Pokedex evokes very subjective texts with "it is said..." kind of information may show that it works by accessing some cloud information that is somehow lost.
The Pokedex in Gen 1 works for the Pokemon of Gen 1, then it is upgraded, people realize there are other parts of the world and so on. The world of Pokemon appears to function via limited access to information that must be retrieved by the players. That is, the Pokecenters work fine, all the technology runs smoothly within the range of what you se, but there is only one ship, one train, Pokemon specialists "just heard of a different continent" and so on.
That brings me to the suspicion that Oak is not doing something particularly new, but asking you to do the laborious work of finding and capturing every Pokemon and having them connected to that particular object of the Pokedex because that's the only way he may access this information that is "out there", that was already computed, but that it is not available, not even for scientists.
cont