I too had a manual checklist like the author and dragged my feet on a proper solution. Now I have a dotfiles repo with a script that installs homebrew, installs

I too had a manual checklist like the author and dragged my feet on a proper solution. Now I have a dotfiles repo with a script that installs homebrew, installs everything in a brewfile, then uses chezmoi to do all my system and shell customization. I’ll eventually get it to the point where I can copy and decrypt secrets, RSA keys, and the likes, as well as support multiple uses (work vs personal) and OSes. The benefit to this is less about new system setup (I don’t buy a new laptop every time the battery goes) and more about synchronizing my settings across machines.