I've had very good luck getting canon printers to work. If the driver provided with Ubuntu doesn't work out of the box, I keep trying drivers for different canon printers, until I find one that works. Hasn't failed yet, though I don't think I've tried your exact printer yet.
The ipod, can't help you with, as I avoid any products with deliberate lock in strategy. There are many fine mp3 players out there. Doesn't help with the current problem though. Have you considered vbox, just for the ipod and the printer ?
David