What are some scenarios that would warrant a decision to under expose or over expose in camera using digital or film?
In the olden days of film, it was said that you should "expose for the shadows", meaning; make sure you get some usable image in the shaded parts of the frame.
With digital, if you blow out the highlights, you are left with no data in the highlights, so I would rather underexpose a bit with digital. (average scenes)
For shooting random scenes with a digital camera, you can take meter readings off the highlights, and work toward the shadows, bracketing a few shots.
If it's a dark scene, meter the most important parts.
For very bright scenes you would want to underexpose, particularly if you are using "averaging" metering because the meter will attempt to expose for an average scene, and it will end up way too bright, often blowing the highlights.
Unless I'm wrong.