I really does not know if this is about searching for a free software replacement for iTunes on Trisquel, on the way one should buy music, so I'll try to answer both.

First, the closest FLOSS iTunes replacement I am aware of is called Nightingale, which is a fork of Songbird, made of a frustration that the original developers stopped supporting/providing GNU/Linux builds. Also, Nightingale does not come with any proprietary parts, that SongBird will ship by default, including addons, with are AFAIK free too.

For buying music, there are many ways of doing so, including, but not limited to buying CDDAs, Vinyls (for exceptional audio quality), and FLAC encodings. I personally does not buy music since the albums I usually want are not available anywhere, so I am downloading them using the Internet (legal in some parts of the world, including the one I live). My favourite website of doing so is RuTracker.org where these albums are usually available.

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