Can you share anything about that one click (nothing to do with one-click™ I'm sure) deployment?
I'm a huge believer in this kind of automation. We make extensive use of TeamCity to drive it. In addition to builds, automated tests, and deployments, we also use it for release promotion and doing other housekeeping tasks like cleaning up data from QA environments, restoring testing databases, etc.
We did have to take an outage for breaking schema changes. Publish to Staging slot stopped, stop the Prod slot, upgrade the database, start Staging, swap the VIP. Total outage was as long as it took to start the VM, a minute or two. We used code-first database with NHibernate.