Help with the move to digital server

I have a lovely system (Krell, BAT Rex, Revel Ultima 2, Esoteric X01-D2, Purist Audio, Siltech), but I want to add an i-pod or a server into the mix so that I can play long shuffled selections of music for casual listening and entertaining at home. Is it for my wife? You bet it is.

Should I get the Wadia i170 and a couple of 160 Gig ipods (1 for jazz, 1 for Pop/Rock)? Or is there a better way? A server that would integrate into the system and play thru my Esoteric with its 3 DACs?

I am grateful for your help. I am open to any suggestions.