I have a similar issue. I already cheated the sim up to the next milestone because I thought it might've triggered with a promotion.
I have all the Expansions, all but the Vampire Game Pack, and all but the Spooky, Movie, Bowling, Toddler, Ice Cream, and Cool Kitchen stuff packs.
I run with CAS clothing packs.
I noticed this was an older issue, but had a Sim start pursuing the Public Enemy aspiration and start really hitting their stride after they could dedicate more hours to their day (the Never Weary Trait, because trying to be a painter/hacker/socialite was straining their exhaustion). I was already level 9 (Net Demon) in the criminal career down the hacker/Matrix style path, by the time I started going down the path with gusto, especially with my budding Fame. By the time I hit the third milestone of the aspiration, I was already at the level 8 or 9 in the career, but not getting credit for already being level 4 in the Criminal career.
It was a lone Sim in the household, and I wish I had a save as it was late at night and I had saved over the issue.
So to summarize, glitched step 3 of public enemy when you are already high up in the criminal career as you start to fulfill the requirements for moving the milestones. I can see if I can make a save where this is an issue.
