Oh if you could give me a link via twitch PMs that'd be nice

You should be able to set IGT as the first time with real time as the second

Jude's story is longer in the beginning due to extra segments, on top of that less fights. Once you reach the prison where Milla is separated, you get a lot less experience from the guards than Milla does, so you end up like 2 levels lower at that point? It's the same up until Milla's "death", at which point Milla would fight only Muzet while Jude goes on to fight literally everybody else. This actually makes you overleveled which is hilarious. The segment is also longer for Jude, and on the end dungeon, you fight Gaius with Milla and Jude as opposed to Muzet, which is a harder fight.

EDIT: Oh right, and Milla's story everybody gets free equipment upgrades except Milla. Jude's story only Milla gets upgrade, so you're also underequipped compared