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I already bought two converter boxes for my two TV sets, since the government was offering a $20 rebate towards each one, and you were allowed up to two $20 rebates.
So, unless my two analog sets decide to break before next February when the switch to digital TV happens, I'm okay.
My understanding is that if you have cable TV, the cable company in effect takes care of the change to digital, and the subscriber doesn't pay. At least, that's how it is with the cable provider in my area of Pennsylvania.