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I use EAC, because I made this choice a while ago, but there are some other tools around, that can even better automate the process of ripping to flac.

Speaking of metadata: Beets does this pretty well. You should try it, even if it takes a few hours to get used to it. There are a few good youtube tutorials.

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Part of the consideration is that I would eventually like to get into the music sharing scene (I have fought this for a very very long time) and there's considerations of which tools and which source of metadata complicating my decisions. Which is the "preferred" among which group?

Beets sounds like it should be part of the mix, but so does MusicBrainz Picard.

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