I use the command line a lot for web dev but wouldn't say I was a real power user.
Pain points for me are discoverability and ease of making dangerous mistakes. I can't remember the command for every useful utility and it's very easy to accidentally break lots of things. Great power comes with great responsibility and all that.
What tools do you use for auto-complete-ish features on the command line? or anything to generally make using it easier.
I personally prefer working on a command line because it's _more_ discoverable to me than most gui's. This did take some getting used to though. The approach is different.
The worry over making dangerous mistakes is understandable. That said I have made very few big ones after a bit of learning, and it has also helped me _avoid_ making dangerous mistakes by facilitating the automation of otherwise delicate or involved tasks which would be unpleasant to click and type through.