I have this dream...trading a Pokemon from gen I all the way up to the last gen, visiting each region
So I made it a challenge and I called it "Seabreak Path" (longest route in the core series).
Rules:
> At least 1 pokemon has to reach the last available gen. If you're able to do it with 6, you're the champion, otherwise just an elite 4.
> Games need to be on cartridge. No Virtual Console or ROM. You can use an emulator and a gen III game ROM only for checking errors in the transfer. You can use third-party tools like Mega Brain and stuff like that for the trade between gen II and gen III.
> Hardware can be modified only for recording and broadcasting progress. If you can't do this, a camera on the console will suffice.
> Prep your save file beforehand for trading between gen.
> Pokémon need to pass through at least one game per gen.
> Progress needs to be recorded or broadcasted, your choice.
> You can get help in this process.
Have fun if you want to partake in this challenge.