Rich's Tongfamily (Richtong.net add-on)

Yes, it does seem that every year, there is yet another update to the Mac that means lots of upgrades, the god news is that if you like you can write a script that does it all. I have one call update-annual.sh that does these things:

1. Operating System update. While you can click on settings to do this, there is also softwareupdate -a -I which basically does the operating system update for you.
2. Update the Mac applications. You are then in a situation where you want all the applications to update, in particular, for Homebrew, you need Xcode updated, so you can should before the update install brew install mas which is the Mac AppStore command line utility and then after the update run mas update which will update all the Mac Apps. Most of these will have specific versions for the new release.
3. Then you have to update brew itself and this means running a script from their site.are
4. Finally, you ready to run an update against all brew packages with brew upgrade

And there you have it!