The reason they're talking about a delay is that more people applied for vouchers than could actually get them, and the reason so many people applied is that the broadcasters lobbied to make the requirements as lax as possible: the limit is two per household, including unoccupied dwellings such as vacation homes. People who own vacation homes are an important (read: wealthy) demographic, so broadcasters made an extra effort to notify these people early. The end result is that wealthy households received a disproportionate number of converter boxes, whereas poor households - the ones that actually need government-subsidized converters - are more likely to be on the waiting list.
There are also other issues, like Obama's FCC pick having a conflict of interest in the matter. (Short of it: Michael Copps used to work for Clearwire, almost the first thing he did at the FCC was to propose the DTV delay, and apparently Clearwire-competitor Qualcomm has a lot of stake in using the analog TV spectrum that will be released by the DTV transition. The DTV delay would prevent Qualcomm from entering many of Clearwire's most important markets for four months.)