User blog comment:B214/Question and Answers 2/@comment-82.40.154.8-20140204164301/@comment-1359322-20140204165321

I don't think High School DxD will reach the point where it'll show Issei's own peerage. Issei would still need a few more years before he could receive a promotion to High-class Devil.

Even after that, Issei still needs to consider lots of factor after gaining the right to form a peerage such as the campaign funds when he becomes independent, it's obvious since it's Issei's own peerage, he won't be able to depend on the Gremory's money. Then he should try to reach an Ultimate-class as well so that he can get his own territory and stuff. Basically, Issei has to do all sorts of preparations to allow him to take care of his servants otherwise it'll be pointless.