OKAY, I HAD TO CHEAT.
I'm just glad that I waited to do the Live Fast aspiration last because even with the proper window installed on the lot the entire playthrough, Josie N E V E R got invited to sneak out in the entire sim-year it took to achieve all of the teen aspirations. The reason she maxed so many skills this "year" is because I was biding my time waiting for the prompt. I got fed up and finally looked it up - turns out, it's a very common "bug", or maybe some shitty rng script.
To add insult to injury, she never had a graduation ceremony. I knew that if she had answered the DAILY calls to graduate early, she wouldn't get the event. It's supposed to be triggered by aging up to adult, so after completing the aspiration, she made herself a cake.
I waited for the following Sunday, which according to the gameplay guides, should have been the date for the ceremony. BUT IT NEVER CAME?????????? I have aging completely off, and maybe that had something to do with it.
I'm fuckin miffed, but honestly? I enjoyed this expansion, even if the working parts are bare bones. That shouldn't be the norm and I'm not here to rant about EA etc but as someone who is specifically doing a save for gameplay completion, it was fun for mechanic exploration. After playing through it once, I can see potential for her future generations.
It also helps that I didn't pay full price for it tho lmaoooooooooooooooooooooooooooooooooooooooo