If you're getting cable of any type you will be ok.
And as katiesue said, the deadline for switching to digital has been set for much longer than Bush has been in office. I think the current date was set around 1998 though the plan to do so was started much earlier.
As for who is making money, that would be pretty much everybody: the government gets to reclaim spectrum it can auction off. The networks get a broadcast format that can be split into multiple channels (you can broadcast more in the same frequency than you could before, for example, I have four different NBC sub-channels I can watch).
And really, the consumer has benefits in ways since one of the reasons we have finally switched to modern TV technology (HD, flat screen, widescreen, etc.) is that the manufacturers were assured of enough future business in the new products that they could justify the R&D necessary (though Japan, by switching to digital broadcast 15 years ago also subsidized a lot of this) to develop them.
Here's a good set of
FAQs about the switchover.