> Where do you draw the line between system packages and user facing apps?

If it works in Homebrew, I almost always pick Homebrew. :) I have a pretty good feeling for what works since for the past few years I've mostly used an atomic distro (Aurora, based on Universal Blue, based on Fedora). It just comes naturally for me on Fedora too.

I've found that this way you can get many of the stability pros of using an atomic distro even on a non-atomic one.