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I plan on taking my Charizard for an adventure like OP's.
Here's what I'm thinking:
>Defeat Platinum Elite Four because I already transferred him up a while ago
>Replay SS, trade him over for the League after my 8th badge.
>Play through SS Kanto Gyms with him.
>Pokewalker adventures
>Defeat SS E4 again
>Fight Red
>Transfer to W2
>Defeat E4
>Enter PWT
Then when I'm done with all that, transfer him to Y. Is there anything I left out? I figure there's no point in bringing him to BW1.