Portable Media Devices - where's my content?

As a long-time lover of gadgets, music, movies, and all things in between, as well as being the proud owner of a TiVo, Media Center, and multiple PMD (portable media devices), I think the battle between consumers, artists, and production companies about copyrighted material and its distribution is very interesting.  My little brother recently got an iPod Video for his birthday and asked me a simple question: where do I get videos from? 

This article is somewhat specific to iPod Videos, but highlights some of the interesting problems that exist around the distribution and reception of digital media, especially given the popularity of PVR's in home media systems.