The CiviCamp session planning met today, and they have put together a fabulous schedule for the conference on September 6. If you weren't already planning to come to DC for CiviCamp, you should check out the variety of interesting talks scheduled.
I started out with CiviCRM as an end user who installed it for organization where I used to work. My colleagues and I were self-taught through trial and error, and after a little while, we understood the concepts and day-to-day contact management fairly well. However, we lacked the opportunity to fully explore functionality before diving in and using it.
Do you modify template files for your site? If so, you ought to know the tedious process of updating all the overridden template files every time you upgrade. (If you don't know that pain, either you've never upgraded or you should quit reading and go check your customized files.)