i don't remember how much this costs... but for me, depending on what i'm trying to learn, i can go either the self-taught route or needing a teacher. I actually do best when i have an instructor to show me then make me accountable for doing it myself.
For those of you with apple stores in your neighborhood, doesn't apple also have free classes to teach smaller groups how to use the programs and such? I remember there was place on the apple site to find this and sign up at a local store...
I used to work for apple and the one to one's were really for people switching over from PC to Mac or they needed help with a specific program, like Final Cut Pro. The "creatives" are pretty knowledgeable when it comes to all the little shortcuts your mac can do. I think it's a pretty good bargain ($99) for a year of classes and they will cover any program or topic you want.
Apple stores also do free workshops but you have to register online at the store's website so that way there will be a guaranteed spot for you!