I feel your pain. Yesterday, after at least three failed attempts to have my Sim graduate, I switched to the back-up save thinking this would help. No. Sadly, my Sim aged up and despite his straight A status, was decreed a Drop-Out! Again. Going off of what others have said, I may well be in your same boat. I went back to day one of my Flashback save, to bring my Sim up the ranks to Global Superstar, which he originally attained in his Teens, so that I could show him in his high school years. I uploaded the family and placed them into a New Save. This after doing the game repair I failed to do after the Patches. He's barely started. Setting up the new save takes time. Originally, I took the time with aging off to get him established before the Patch and the release of HSY. He made it in ten Sim days as he did in my Main Save. And, he managed to win his first Starlight Accolade for Best Song. In fact, he got the three he originally won while in high school. He couldn't get the fourth nominated, which was a clue something was amiss. This, plus the Drop Out status is what sent me to the Back-Up, or Plan B. Which bore little fruit. He still managed to achieve Drop Out just for aging up.
I don't normally do stuff beforehand like that and now it seems it was a useless waste of my time. Glad I created a back-up, but that seemed bugged, too. :open_mouth: I do hope I won't have the groundhog day bug, although to a very limited degree, I've experienced it. Being a Rock Star in the making, he writes songs, too. Used to be, if a Sim couldn't finish it in one sitting, you could click on the sheet music held in their personal inventory and resume. There is no resuming going on. Instead, you get to start it all over again. Face/palm. Writing music, like writing books, takes a lot of time. Sim hours, in fact.
The good news is that by taking him back to the beginning and transferring the family into a new save, Erik still won his first Karaoke contest by the same points count: 86/100. I have some hope. I managed via MCCC, keeping his needs full, to have him finish the song he won his first accolade with. Time will tell. If things don't work out as I had hoped, at least I've shared several updates on the What Happened In Your Game Today thread, to serve as the Flashback story. I just hoped to include pictures from his graduation. (I was seriously deliberating whether to redo his wedding to his high school sweetheart, but now, I'll just be happy to show his graduation.)
Hope you don't mind me joining your rant.