[@fluffyNES] The group RPs that I've been a part of (they weren't on this forum) were very large scale and generally had upwards of fifteen to twenty members, so I'm afraid my opinion would not help with this part of the planning.
Maybe we could let each person have a chance to RP the Outsider? For example, when he makes an appearance the first time it could be you. Second time, [@Wade Wilson]; third, me; and so on and so on. Same with any character(s) like Granny Rags or the leader of the Bottle Street Gang.