Troll the Web all you want--you'll almost never find price breaks on iPods. Unless you go straight to the source, that is: Apple's own outlet store sells refurbished players for pennies on the iPod dollar.
For example, you can snap up a 4GB nano (last year's perfectly cromulent model) for a mere $99--half the original selling price. Other current bargains include a 1GB Shuffle for $49 and a 30GB video
$199 $179. I say "current" because the deals and availability change on a fairly regular basis. So if you see something you like, don't wait to pull the trigger.
To Apple's considerable credit, refurb iPods carry a one-year warranty. If you don't mind last year's models, the deals are impossible to beat.