I finally returned to my regular save with updated mods. I noticed my sims have gained some milestones. But some of the milestones only seem to take the current situation into account. My supersim has been a vampire, a werewolf and a mermaid in the past and is now a spellcasters. She only gets the spellcasters milestone. Her boyfriend had a job but quit before I patched the game. He has no work related milestone because he is unemployed at the moment. The milestones don't remember past jobs.
Well at least they both got the milestone for their university degree.