..I thought I'd have one last go at trying to simply get a Nano to talk to it. After wasting an hour or so trying with the pathetic instruction set, it turns out that because I have 10.4.7 my Nano won't work. Of course I had to find that out for my self by searching on forums like this. OK so I try to update the software but I get an error message saying I can't connect to the update server (internet connection is just fine). I try my local Apple store who say that the only way to get the update is to connect to the server. That's in the chocolate teapot category of help I feel. Or I could buy a whole new OS for more than the cost of the Nano. Yeah right. I google "download 10.4.8" and get some links to the Apple site but the click throughs from Apple's own site don't work. This is now way past amateur hour. Does anyone have anything that might help. I know this is heresy but if I connected my nano to PC it would work a treat, but it's my son's nano and his I-mac so that's not an option and i have my own I-tunes on there any way. I thought these things were supposed to by easy to use?