I get the value of leaving XP behind. I also get the pain and potential expense involved at the family level. Like many of you I just bought my Mom a new machine and did my best to move all the stuff she needed over to the new one. Not everyone has the money, time, or skills to do that. Moving to Windows 7 on the same hardware is possible, so I wish that there was some $19 upgrade to a minimal version of Windows 7 that could be done in place.
Cloud based storage (dropbox, skydrive, google drive) should ease this pain some going forward. Should we start to point our not-technical-at-all friends and family to something like Chrome OS?
It's different at work, at least some. There are often compelling advantages to moving to a newer version of hardware or software. It feels like it's only moderately painful as long as we do it often, the five year gap between SQL 2000 and SQL 2005 allowed a lot of inertia, debt, and complacency to set in.