A guy at work was having trouble with a 4G iPod that his son didn’t need anymore. He said he couldn’t sync it with his PC because it was formatted for his son’s Mac. I told him to bring it in and I would try to fix it. I didn’t have a problem syncing it (it was already formatted for Windows). I had an old program that was an iPod Updater that I tried to use to restore the iPod (wipe it out and completely reformat it, using the latest iPod software for that model), but that capability has now been built into iTunes. But iTunes wouldn’t download the update for the restore even after I uninstalled the obsolete Updater. I gave him his iPod back and said it should work fine even though I hadn’t restored it.
A few days later I was trying to make my first iTunes purchase since November and they wouldn’t download either. I played around with my firewall settings in McAfee (even turning it off completely), but decided the problem must be with iTunes timing out before a dial-up connection could bring a song over (about 10 minutes for a song). It didn’t help that iTunes was now trying to download three songs at a time instead of one like it used it to do. I tried some different settings in iTunes, but couldn’t fix the problem.