Sure. I do this with yt-dlp + plex.

These are containers not VMs. Just rebuild them. Rerun docker compose or docker run on the new machine

Wheres the cost/benefit justification? My company went through the certification process. It cost many thousands and took many months.

im in the calibre club also. It can trans format and even edit.

back everything up and do your update

simple

Looks interesting and Im looking forward to giving it a try

Yes and that definitely would not stop me from looking

I would do a search for *.sqlite