>>12997608It has a bit of a timeline, though some things don't really make sense when you think about it. Gen I and III happening at the same time, with Oak apparently giving Birch a Pokedex.
What makes a bit more sense is that Gen I happens as normal. Then you have Gen II where Oak sees potential in the protagonist and gives them the Pokedex he's been working on. Then, when the protagonist is adventuring through Kanto, Oak gets the idea to expand a bit more on the Pokedex and gets into contact with Birch. This would make it that Gen II happens two years later, and then III happens within at least half a year after II starts. Since it's understandable to think Oak would prefer to first keep such a prototype device closer to catalog more Pokemon close by.
Then after all of that, Oak gives Rowan some Pokedexes as well... or he gave Pokedexes to both Birch and Rowan around the same time.
But eh~ None of that has been canonically stated, so it's pretty much just a random musing.