I just finished migrating my blog here to windows 2008 -- I am testing to make sure that I can indeed post an entry.
The migration wasn't bad though there were definitely manual configuration tweaks that had to be made. Interesting that MS released such breaking changes... progress!
I had to manually move the registered httpHandlers and httpModules into the <system.webServer> section and rename the section tags to "handlers" and "modules". I also had to enable detailed errors to figure out what was going on.
Enabling Detailed Errors: Click Here
Breaking Changes Reference: Click Here
Thanks to Mike Volodarsky for the great info!