I've had to setup at least 5 new macs for dev from scratch, and each time it was a pain.
The last time I decided to do something about it. I tried to find a faster way of installing apps.
So I built a Workflow for AlfredApp, that taps into brew-cask repo, that's community driven and lets me install every app in there with a simple progress bar.
Can be downloaded here : http://altryne.github.io/install_apps_alfred/