[mikemcquaid]

The officially supported thing is: https://github.com/Homebrew/homebrew-bundle

See my Brewfile in my dotfiles for how I use it to install my stuff: https://github.com/MikeMcQuaid/dotfiles/blob/master/Brewfile

If you want to go a step further there's also Strap which will bootstrap your macOS system with some sensible defaults and install Homebrew, your dotfiles and your Brewfile: https://github.com/mikemcquaid/strap

Finally, if you're interested how I combined these to replace Boxen at GitHub (our macOS system/project bootstrap tool using Puppet) read this: http://mikemcquaid.com/2016/06/15/replacing-boxen/

[Singletoned]

This is utterly brilliant! Thank you.

I've been looking like this for quite a while. I'm still looking through it all, but I don't suppose you have a solution for setting System Preferences, particularly Trackpad settings and remapping the Caps Lock key to Ctrl?

[mikemcquaid]

I don't use it but https://github.com/benbalter/plister should do that. There's an open issue to integrate it with Strap, too: https://github.com/benbalter/plister/issues/2