It takes me an evening just to figure out what all needs to be reinstalled. True, if it's something you don't do very often, it can take quite a bit of time just to get the proverbial ducks in a row.
I just did a mental count - since mid 2007, I think I've done about 20 reinstalls involving the O.S., SQL Server, Visual Studio, MOSS, etc. (Now, some were for machines for other people, some were VMs of mine, etc)
I'll say this, I've been using Windows 7 for about a month or so, and I REALLY like it. I've figured out how to run a single instance of SharePoint Server on Windows 7, so I don't have a need anymore to run Windows Server on my machines....so I'm circling back to put Windows 7 on all my machines.
The new UI features in Windows 7 are certainly nice, but what impresses me the most in Windows 7 is the speed and snappiness. So far, knock on wood, I've had zero issues with Windows 7, and I've been beating on it pretty hard.