I must have been a good boy in 2006: Santa brought me an iPod video! I have been using iTunes for quite a while and never upgraded to version 7, but the iPod video comes without software and requires iTunes 7. Ok, I thought, how difficult can it be?
At 1 a.m. I was ready to kill someone. The software upgrade just would not install. When it came to installing QuickTime (as part of iTunes), I hit an error 3. Over and over again. I uninstalled, scrubbed, cleaned the registry, installed QuickTime by itself before iTunes all to no avail. Finally, just before 2 a.m., I found this post in The Incrementalist. It did the trick and I could go to bed.