Well for me I would HAVE to make a new character, so I guess that isn't a problem for me, but some people have microtransactions on their characters that they can't transfer and might not be down for that. But I can totally go for something like that.
Being some one that did a lot of RP, and the story of the game, the story should be rather open and simple for the guild. But we could keep it deep by constant updates on stuff we do. For example a mercenary group of adventures. We help who we want and so forth, saying we are payed for any missions or anything like that…