I just watched a good interview on C-SPAN with Representative Rick Boucher, who represents the Virginia congressional district I grew up in and sits on the subcommittee with oversight of the transistion.
He mentioned several issues that are beginning to come to light regarding the transition, including the possibility that some viewers in outlying areas will have to replace their outdoor antennas to pull in digital TV signals.
The YouTube video is embedded below. The first 10-15 minutes are the most interesting.
