I just gave my sim the Family career. He never gets any family lit books, and sometimes he gets stuck at work indefinitely. I used MC to give him 3 levels of the assassination skill when I started playing him (He's a serial killer in my town), I dunno if that may have something to do with it. Whatever is going on, it isn't throwing any script errors. Any ideas what it might be?

Is it a combo rabbithole I've had problems with those and custom careers and schools
Or you could try replacing the rabbit hole by first making a copy of the RH and saving it to the bin bulldoze the original place the copy do a Save As exit the game and clear the caches your sim and all sims who used that RH could lose there jobs though

Thanks. Sorry I didn't respond earlier. It was a problem with the save game. I loaded a backup and it worked properly.

As I recall, The Family can have issues with sending employees home on time. Whenever I notice that happen I just reset the lot. The family literature comes in around level 4 in the career, but the frownie face mood indicator for having it read starts sooner. Ignore it until you actually have the books to read. I've gotta leave for work right now, but if you have other questions about the career post them and I'll check in this afternoon.