Brew is not even tech-person friendly. I'm comfortable with the command line and I had a ton of problems getting cask to work. I LOVE the idea and I will use it every time I setup a computer, but there's so many issues to work out. Mainly, some apps not updating correctly, the storage of app versions in cask, settings, licensing. It's a mess.
I really hope it gets better. I'd contribute if I was knowledgeable enough to do so.
Be aware that Homebrew Cask [1], which your comment is referring to, is a separate project being built on top of Homebrew ("brew") [2] and it currently has a number of shortcomings that are independent of anything to do with Homebrew itself.
I really hope it gets better. I'd contribute if I was knowledgeable enough to do so.