For people in this situation, there's a product called PCMover from Laplink which we've used successfully on a lot of migrations. It can do XP -> 7, with docume

For people in this situation, there's a product called PCMover from Laplink which we've used successfully on a lot of migrations. It can do XP -> 7, with documents, settings, and installed software, usually with almost no trouble at all. It's well worth the 50 bucks or so. Unfortunately, the product has a bug that completely kills software updates in Windows 8 systems, and even after we had purchased dozens of licenses of their software and gone to the trouble of narrowing down the scope of the bug to a "definitely a PCMover bug" range, their support personnel refused to look into it and pretty much told us to take or leave their product. So we quit using it, since we're trying to get all of our XP-using customers to skip 7 and go directly to 8. But yeah, it's a much bigger pain in the butt for a lot of people than a lot of people seem to realize.