Brian Sherwin has posted up an insightful piece about VSTS not being able to help you unless you change your habits. In many respects Team System is a bit like SAP (except heaps cheaper) in that it offers an amazing opportunity to customise and thats what a lot of early adopters are going to do.
Once again, like SAP users, VSTS users are going to hit a stumbling block, but in this case I don’t think its going to be upgrade blockers, instead I think its going to be the fact that they have tried to graft their old processes onto a product which may have served them better in its default configuration.
One of the things that I have tried explaining to people is that VSTS provides an opportunity to reduce the dead tree usage in your organisation and store design and project management information as first class (and strongly typed) entities in the various TFS data stores.
If you insist on using the tools the way that they are supposed to be use AND continuing to produce your out-dated design artifacts then you are just wasting your time.