Fair enough, I agree it would be hard/impossible to make a full outfit progression "make sense" for players with complete saves, since the girls are already corrupt. Unless, they add a reset button for that character. This way we could fully experience the new job/outfits and they could even add a booster making you progress faster.
I'd prefer they make a girl work 1 or 2 more jobs and develop full outfits for them in each update. The stories that go along with the job/outfits don't need to be deep, especially initially. My opinion might not be the norm, but the increasingly slutty outfits are pretty much the sole reason I'm invested in this game.
Eventually, my hope is that we get the best of both worlds, where the girls work many or all jobs and have outfit progression for each one. This way, we can restart the game and watch the progression happen naturally.