There seems to be a developing meme that upgrading (in place) to Windows 7 is problematic; here's Dvorak on it:

Windows 7 upgrades are so complex that they can reportedly take up to 20 hours. The consensus amongst users is that the best way to upgrade is with a clean install (read: by removing everything). To me, a clean install is not really an upgrade—it's just putting a shiny new OS on an old clunker. A true upgrade involves installing a new OS on a system with all of the old data intact. Everyone says Windows 7 is no good at this.

In place upgrades are what most people do. Sure, we should do a clean install, but seriously - who has the time? Even if you have good backups, getting all of your old applications re-authorized (especially on Windows) is a royal pain. Until Snow Leopard, I thought Apple did a generally decent job of this - my upgrades (across 4 systems) from Tiger to Leopard went smoothly. Snow Leopard has been something of an issue on my Macbook though.

I had to change Time Machine to less frequent backups (because it would freeze the UI every time it started up). Many of my applications crash when I close them. Now admittedly, that last one is just a small annoyance, since I'm closing the app anyway - but it gives the OS an unstable feel.

The bottom line for me is this: Unless someone tells me that a Windows 7 upgrade is blowing data away (there's a nasty bug for Snow Leopard that does just that) - then I'll just chalk the tales of trouble up to the diverse set of hardware and software endpoints that Windows encounters "in the wild".

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