Yeah...

It works better for some cuts than others. This weird off-axis cut for example doesn't give the result you would expect. Reading Michael's description of how the command works, I see now why that's the case.

"Later on I want to have some additional methods that will take these potential silhouettes and figure out which pieces of them are hidden and which pieces are visible."

This would be amazing. Does Rhino currently have something like this? I have access to it at school...

The attached image shows the cut on the right that was performed with the silhouette command (the one on the left is the one I traced and how it should look from this perspective view).