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Whether to have Calibre locally installed on each machine is a matter of preference. I have settled to keep all apps in /Applications for security purposes, easier to manage. I also set ownership to root:wheel to avoid issues. But calibre certainly works from a portable drive. Note that it will still keep its preferences in `/Library/Preferences/calibre. You would need to replicate that on each machine as needed or use a folder on your portable drive with a symbolic link in ~/Preferences.
I keep my calibre folder in home as ~/calibre and use iCloud for backup and sync between systems. I use ChronoSync to keep the folders in sync. This allow me some security in case I mess up the local folder.
The calibre library itself is self-contained in its data folder.
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