What's the point of homebrew cask? Why is it any easier than finding an app I need and installing it normally?

Same reason people love package managers in general. A single bash script can install all the programs you want. Add Homebrew Cask and even your GUI apps can be included in that script alongside wget, vnstat, whatever.

Makes sense to me! Probably not worth re-installing programs I already have, though, would you agree?

Yea, I only do a "brew cask search" for new apps I want to install. I believe you would want to avoid attempting to re-install an app via Cask that was installed normally (~/Applications vs /Applications). Personally, I would do a clean install to transition an app to being managed by Cask.

Hah, I was going to ask if they planned to add a formula to homebrew-cask so that I could use it to install Cakebrew.

I checked cask before I downloaded Cakebrew. :P

I agree. Isn't Homebrew primarily used to install CLI tools? Sure you have things like compilers/programming languages, but with the frequency that you install those types of things it doesn't make sense to use a dedicated app.

For somebody with an aversion to the command line I think the only reason to use Homebrew would be Cask.