A: 

I usually copy additional files to output using Post-Build event, but your excellent question made me question my ways. I found that if you right-click on item and choose properties, a different dialog shows up, which allows you to specify what operation to perform during the build. However, I was not able to create a behaviour similar to what you want using standard windows commands. So you likely would need to write your own program to copy files to output.

Juozas Kontvainis
I had thought about doing it this way (via post-build) but I had figured that this is a simple operation and should be doable in the normal build. Interestingly I cannot find anything about this on MSDN or their forums... a true mystery.
Zack Mulgrew
Ended up writing a script to copy the files and executed it with the post-build event...
Zack Mulgrew