maybe, just maybe Copy Trans Manager? It is free and does not use iTunes. Is your iPod taking a charge when you install it to computer? If no, I do not know anything that will help.
'00 Safari SLE with '95 4bolt 355 LT1; decked .010'', hand ported 374s & intake (David Vizard tech), 1.94/1.5", farmed out EFI 24x, 2001 LS1 pcm, VooDoo 211/219*, w/1.7" rr .574"/583", 4L60e, shift kit & corvette servo, G80 GT4, 3.73:1, ported & massaged Granny's Speed Shop headers, true duals, 2 long Cherry Bombs used for resonators, 2 long Thrush Turbo mufflers, local tune under an Oak tree. 5 year project/swap.