I'd just be happy with the expansion before that, TDS, not being completely locked out behind 6 year old progression.
Only the requester needs to do group progression(which is molo-able) I think, and if each raid gives 4 click-flags, then I don't see raid-keying being an issue...You should be able to do a complete expansion clear in one go, without flagging issues. Now, if only they would fix the brother island boat on AB...