Nice post :) Thanks for sharing!
I shared an article a while ago explaining how I evolved my install script into an update script to never run into the issue again of having a stale script that doesn't work on a new machine:
Also, my personal preference is to keep, both, my setup script and my bash config so simple that I'm not afraid of breaking it. I put all bash configs in a single .bashrc file to make it straight forward to find anything and change anything when I feel like.
No matter how we organize the files, I think the point I'm trying to make is, that dotfiles are a living thing which we adjust constantly and we should minimize the friction to change as much as we can :)
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