Scoble is wondering what Microsoft could do to evangelize Windows XP to users of Windows 98. My comment entry was getting a bit long, so I will post it here instead.
Ask the average user and they have no clue when the support life of Windows 98 ends and why that might matter to them. I assume that Windows 98 users are mostly home users. The real question is will my stuff still work, how much will it cost me, and is all this change worth the chance that my stuff will not work as it is supposed to?
What are the Windows XP sales channel breakdowns? Home vs. Pro? OEM versus retail?
I would target families wanting better control of individual experiences on their shared computers. Everyone has their own accounts, you can set up quotas, only the parents can install new applications, etc. With multiple logons you can keep one person’s connection alive while still taking care of something else in your own space. Windows XP allows for a more complete entertainment experience to keep your kids happy even with the lockdowns. Play on the fact that this OS is frequently kept up-to-date and expanded by service packs that are really like an OS upgrade.
Most people find it annoying that Windows Messenger is there by default and asking you to associate yourself with a .Net Passport. How many people register their copy of XP after they activate? What about this distrust leads you to believe they want to sign up for a Passport too?
Assume the upgrade user takes a trip to Best Buy and looks for more information on the upgrade. What reasons are you giving him to spend his $90 and take the chance of everything not working the way he wants? Common tasks, visual cues, music jukebox, movie maker, redesigned Start menu. Nothing overly compelling. How does it make my computing experience more reliable relative to the old ways? What does it bundle that saves me money and hassle of integrating other apps?
Windows XP makes me more secure, reliable, and gives me the most current features. Emphasize the new more secure underbelly. Offer a family pack like Apple. I would also like to see a Windows XP Home + Office for Students and Teachers bundle at a discount, similar to the desktop license for a business.