This is outright awesome, for the record. Please continue exploring these scenarios. They're really interesting and you're clearly thinking them out really well.
I don't have the time to contribute quite at this moment, but before one of you comes up with it, I'm calling dibs on Pokemon not being released for the Gameboy in 1996. Although I'm not sure what exact difference I'm referring to, there are a lot more wide-ranging effects for this than you'd think. Especially with Nintendo's "never made a loss" reputation being singlehandedly supported by Pokemon during the sixth-ish generation and Nintendo's handheld stronghold being so severely weakened without it.
“These are my principles; if you don’t like them, I have others.” – Groucho Marx
