We use automatic deployment to all our environments. No real pitfalls to watch out for. I know many use MSDeploy/WebDeploy together with TeamCity/TFS. For configuration files we use SlowCheetah, many also use OctupusDeploy to simplify this even more.
We are using MsDeploy for delivery with Teamcity.
However, we are still investigating, if there is some easy to implement solution to deliver content
Varies slightly depending on where it's hosted (and said hosting partners "rules"). But usually jenkins/teamcity for CI stuff that uses psake for various build/ci related tasks. Lately we've used Octopus which has worked very well. In cases where that can't be used we've also done deploy using simple powershell scripts. For configs I've used the one that ships with VS (paired with slowcheetah to actually make it useful) but I prefere the XmlMassUpdate from the MS Build Community Task project.
We currently use MsDeploy for deployment, SlowCheetah for xml-transformations and Jenkins for build. Would probably prefer Teamcity but our company hosts a centraliced Jenkins. It does its job but its not as slick as Teamcity.
Im hoping to be able to take some time to look at Octupus deploy in the near future aswell.
I've tried Octopus on a previous project. Really nice that you don't need to connect to the server and do the copying yourself. If something goes wrong, all you need to do is to back to the previous release.
Big stress release!
What tools do you use to deploy your EpiServer site/project?
Do you deploy manually or automatically?
Any pitfalls to watch for?