One of Microsoft’s biggest challenges with Windows 7 is an easy upgrade path for consumers and corporations. As this chart illustrates, it’s a mess: Only a few upgrade paths qualify for an “in-place upgrade,” which means you can keep “files, settings, and programs intact from your current Windows version.” Most will require a “custom install,” which WSJ gadget guru Walt Mossberg describes as “a tedious, painful process” for “most average, nontechie consumers whose PCs have a single hard disk.”
I’m reminded of the 2006 If Microsoft Designed the iPod Box parody video. Commissioned by Microsoft’s own packaging team to humorously educate their marketers about the pitfalls of packaging & branding, it’s not really looking like they’ve learned the lesson: