I learn things by not being constrained by what I know. At the moment, I have never used Powershell. If I needed something done and I thought Powershell was the right answer, I'd just build it and learn as I go. You don't need to be an expert, you just need to build good (not perfect, but not clunky ;-)) solutions.

When SQL 2005 came out, we had a project to convert a 2000 db to 2005. There were a bunch of DTS packages and I estimated 40 hours to convert them to SSIS, then I just figured it out on the fly. I didn't use configurations for dev, test, and prod connections, which is a standard that has been introduced since then. Our SSIS development has changed a bit since then, but they worked.