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That reminds me of this older "History CYOA" by phylogenik on /r/MakeYourChoice, specifically the first option, the "Council of Greatness". You could definitely accomplish some major things, but it would take a lot of work (and you will generally find your results tilt more towards the soft...
Maybe I just speedread through and missed it, any reason why Anko isn't coming with them? You would think that leaving the village would be a prime time for the Man in Green or whoever to strike, from Konoha's POV at least. So they'd want Anko along in case that happens.
So, with that in mind, how are you going to write him now? I assume he's still going to have the same flaws as before, but if that part of you is dead, I feel like you might struggle to put yourself into his mindset.