Deploying can't get much easier than clicking a single button in VS.Net... Rolling back IS an issue but it can be mitigated by versioning one's source code and testing the site locally before deploying.
every single change had to be accompanied by a full and tested rollback script, and given often the deployment was messy (lots of integration/hardware mixes/etc) writing these was difficult and time consuming. ... but, they saved my arse on more than on occasion.
moral of the story: always have a backout plan. Stuff goes wrong. not often, and if you're good, then rarely, but when it does you need a way out.
There was, however, a working version of the code sitting in the directory alongside this horrifically broken monster. I knew the configs were correct because they had been working not 5 minutes ago, and I hadn't changed them. So I updated a symlink (this was on Linux/Apache, but it would apply on IIS/Windows too), and everything was happy again, though using a slightly older codebase.
How hard can that be?
Evidently very hard. Despite spending the entire evening trying to get them to communicate and push files, it simply didn't happen. In the end I ended up writing my own deployment-system based on source-control, Samba and rsync in Bash. It was easier, it worked and I know why it works.
If that is easier to get working than a "one click" solution, the authors of said solution better get a bigger button. I can't seem to click this one.
Apparently there are some bugs which prevent parameterized deploys from working properly. Also, the documentation for Microsoft.Web.Deployment is very poor.