Going from DVI to VGA means a digital-to-analog conversion, and at that point you are trusting the converter to have better video DAC's than whatever DVI-equipped source you were using. Granted, HD cable boxes aren't necessarily going to have the world's best video DAC's, but I'd be hard pressed to convince myself in this case that $500 would benefit me. The one case where I might find a DVI-to-VGA device compelling is HD-DVD or Blu-ray if studios had started using the ICT to limit resolution of component video outputs. Since that hasn't happened, I'd tend to stick with analog video in your case.