As for the whole digital TV, convertor box issue, well...
When I was in Richmond, Steve found out that he could actually get the digital HD signals via a set of rabbit ears he had set up.

I think one of the other concerns with the proposed delay/postponement, is that it could end up getting delayed and postponed again. And again. The local TV stations/affiliates have already done their conversion - and spent a lot of money doing so - and in many areas, a lot of stations are already broadcasting in digital/HD in addition to their regular analog signal. The local stations don't want to be "wasting" money by having to run both their analog and digital transmission equipment at the same time.
There have been lots of new commercials lately, and many stations have also run "Are you ready for the switch?" tests where they've turned off the analog signal for a brief period of time - usually during a newscast - and if you stopped receiving a picture, well...
DR MBarnum - Your compassion is not misplaced, but, at least from all the TV commercials and newspaper articles I've seen in NYC and in Richmond over the past year, the upcoming switch to digital should not have been a surprise to anyone. And, unfortunately and inevitably, even if the switch does get postponed, there will undoubtedly still be a number of people "surprised" when it happens.