Just quick thoughts, How old was pein when he was leading the akatsuki? he looks in his early or late 20's, We know itachi was a member since 13 years old, That means Pein was about a 18 or even younger since it would take awhile to gather the members. Thats pretty crazy, Just a thought.
Also, if the rain village has been in civil war with pein being a leader of one side, does that mean there is a opponent just as strong as pein on the other side? It seems the sides are in gridlock.