This week Monday and Tuesday I'm spending some time at the Chicago Microsoft Technology Center with AngelaB and a lot of other great expert on TFS/VS 2010. We're working on upgrading TFS 2008 to TFS 2010. I have to say it’s much easier than I even imagined! MSFT was attempting to make the installation so easy that you don't have to read the installation documentation and they have succeeded! Everything is very intuitive. We even brought in our own process template and that was migrated w/o a problem.
Things I’m loving about TFS 2010:
Hierarchical Work item types
Simplified DB model that makes projects much more portable
Easy Upgrade/Import from 2008/2005
When it releases, it’s going to be part of the MSDN license
Although TFS 2010 is still in beta, the head architect and I have decided that we'll be upgrading to TFS 2010 next week.