You might have a bit of difficulty there. The software bundled with an iPod is called iTunes and there are only versions available for Mac OS X, windows XP and 2000. You could try installing iTunes on ME and see if it works, but if not, I believe there is other third party software available like XPlay. I don't know how well this works and I think you have to pay for it too. The other difficulty you may run into is USB support, the fact that you are using ME means that your probably have an older PC and you motherboard may only support USB 1.0 and not USB 2.0 or firewire, its not likely to be a big issue but you may have to put up with relatively slow transfer speeds. Not a major irritation though. Personally I run XP at home and 2000 at work and reckon both are far superior to windows ME, however you need a reasonably powerful PC to run either comfortably.