If you miss the events, the patch will give you a prompt to at least let you get the Vanessa stuff, but yes you lose the nudes / visitation.
Kali's fast track is entirely her father's fault, which is something she points out a number of times makes things feel like she's "cheating". She gets into school, gets accused by other students of using her father's influence, finally proves herself to the other students, works on a project together, aaaaand basically proves them right when she gets the job and they don't get offered anything because it was all for show.
Kali should still be a student, but her father wants her working at the company, so he made it happen. She could have declined it and remained at school, but I doubt that would have stopped him coming up with another scheme since it's been a running theme since he was introduced.
With the recent story events, I can't help but wonder if he has an ulterior motive that he's hiding under the guise of "inherit the company".