I've been testing this hotfix for about a week, and it has cured a good chunk of my usual VS2008 crashes. Specifically, if you undock any windows withing the IDE, or change the layout, VX2008 tests to crash the next time you enter debug mode. I tend to change my layout a lot when I switch between working on C# mid-tier code, and into Data Dude to work on data generation configuration, so this one hit me a lot!

Download the hotfix here: KB960075