TFS 2008 Setup/Admin: Lipstick on the pig
After leaving the version control team to work on the freshly created admin/ops team, we ended up taking over setup (for better or worse), so that first year was trying to make Orcas setup something at least slightly more palatable than Whidbey's. We also tried to make those things that were not- or kinda- supported in Whidbey work a bit better, especially at setup time (analysis services on a machine other than the normal data tier, for instance - reporting services on a machine other than the app tier, WSS 3.0 of course, etc).
We're in the middle of working on vNext's story and while there's a lot of hope and cool things we're getting done, there's not a whole lot we can say about it just yet, but I wanted people to know that none of us consider the Orcas setup story to be the way it should be. It's certainly an improvement from Whidbey, but we want to do better in the future... a lot better.