I've never needed the option of serving coffee/espresso to the headmaster before the tour and dinner has always been enough. Just curious on the coffee business is that something that is only available during this scenario? Cause my Sims slurp up espresso like nobody's business and the "serve" option only ever gets me producing two cups. I've never been able to get a visiting Sim to take the 2nd cup and I don't see another command for it.

Just one of those things I wonder about sometimes.

In my experience, if the headmaster is in the room when you serve expresso or make drinks from the bar, he should automatically go up and take one (if someone else comes in and swipes one, you can just continue making them until he does).

Don't serve espresso while everyone else (including the headmaster) is sitting around the table in the other room. Otherwise he won't go for it...basically the headmaster follows your Sim around like a little puppy dog. I found that out today...I simply had the father take the second cup and have the mom serve up some more, problem solved.