Just randomly thought about this, but the life of the portraits must be horrible. You just stay and look at empty hallways most of the time. Sometimes you go and visit other paintings and get drunk like Violet? with the Fat Lady. How does that work btw? Does the liquor, food etc. just spawn back at some point if they consume it?

And the old headmasters? They just stay and sit in their paintings for days. One of the old chaps was even painted with horrible hearing, who is that cruel for real? If they want a change of ordinary they can go and hang on a painting hanging on an empty hallway or abandoned home.

And they all are aware. All the time.