I choose the pieces I want to educate the audience with based on me thinking they are pleasing and hoping that I'll be able to show the audience why so that they'll enjoy it too. Maybe that means we're on the same page?
More or less, except that I prefer not to think so much about "educating the audience". To be honest, I don't much like "pleasing" either. I reacted to your previous post because it sounded a bit like you thought "pleasing the audience" could not mean anything other than playing extremely famous and popular pieces.
As regards education, I think what one should mainly think about is educating oneself. If you keep studying a wide range of repertoire, you will inevitably find some lesser-known but great pieces that you will want to perform to an audience.
When you arrive at that stage, I think it's wise not to think "Let's play this to an audience to educate them".
Instead, you could think: "How will an audience feel about this, considering they have probably not heard this work before? Do they need to be 'educated' in some way to really appreciate it? Perhaps I should make a spoken introduction or write some program notes? Can I pair it with some other piece to enhance its effect?"
These questions get more important the more unusual and aurally challenging your piece is. Let's say you had been able to educate
yourself into actually liking Schoenberg. In your audience, there will probably be a number of people that are still like you were before - they
know that
Schoenberg sounds like sh*t. What you need to do then is not to "educate" or "please", but rather to "convince" or "win over".