I can't imaging how any government-sponsored (i.e., forced) program such as the conversion to all-digital TV in 2009 could cause anything but confusion, frustration, and anger. This Ars Technical article discusses the topic, but of course doesn't go into the real issue: government should have absolutely nothing to do with such things.
Only the market should determine when and if a conversion from one technology to another occurs. When government does so by force, it by definition bypasses the millions of decisions that individuals would make--including whether or not to spend their money on technology that they may or may not want. It represents not only pure coercion, but also the confiscation of wealth.
And, if flies in the face of reason: how can government possibly determine the date by which the appropriate technology will be developed? With manufacturers rushing to meet the deadline, it's almost inevitable that potentially better technologies could be developed if more time were allowed (which the market would provide).
Government has one function: to protect our individual rights. Anything beyond that, including deciding what kind of TV we should be watching, is illegitimate and the cause of every economic dislocation we've experience over the past 100 years or so.