I am trying to do this but I can't get the "go 5 days without deep drinking" to start. Do you have to take a deep drink first and then stop? My Sim has never taken a deep drink so maybe the timer do...
Well one thing I was doing was switching aspirations. I played a new game and used this aspiration from the start and it worked fine. The time started and I got the full five days. So I must have done something in the old game to disable the timer. I did use the aspiration milestone cheat to move the game along.