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There are some old questions surrounding this topic, but the landscape has changed a bit in the last couple of years. I'm looking for some fresh answers.

Why I'm looking
Over the years iTunes has become increasingly bloated without adding much of anything I care about. It looks a little slicker in some ways. Less usable in others. Like the iPhone, it's just not that exciting any more.

Where I'm looking
I'm considering two primary alternatives (Tomahawk or DoubleTwist) and one outlier (Songbird, whose future seems shaky to me).

What I've got
I have a large-ish library of mostly AAC files (around 65 gigs). I have one iOS device (iPad, which I hardly use) and two Androids (an Android 2.3 phone and 4.3 tablet). I listen to my library mostly on my MacBook Pros (10.6 and 10.7). I have extensively rated, categorized, and tagged (via comments) my entire catalog and I use this data to create detailed playlists.

What I expect
I'm looking for something that is focused on an ordered library and listening experience; maximizing compatibility and sound quality; and killer application performance. Integration with services like Last.fm (personal fave), Pandora, and Spotify is a plus.

What have you found?
Has anyone here successfully made the break? Can you help those of us who long to escape the Apple ecosystem, even if only for a minute?

Bottom line
Have you made the switch successfully? If so, what app did it for you and why and can you share your tips with the rest of us? Moving a music library around is a big effort and I would love to learn from your experience before diving in.

marked as duplicate by user10355, daviesgeek, nohillside Aug 16 '13 at 6:51

This question has been asked before and already has an answer. If those answers do not fully address your question, please ask a new question.

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    Thanks for the question and for putting some time into laying out your thoughts. It's still a bit unclear though if you are looking for software recommendations (because you seem to focus on three applications already) or for war stories of people who have moved away from iTunes. Can you through some light on that? – nohillside Aug 16 '13 at 5:12
  • Does that sound better? – plainclothes Aug 16 '13 at 5:58
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    Uhh, I'm not so sure about the edit, "What is the iTunes killer that has the right mix of support, performance, features, and likelihood of being around 5 years from now?" is not answerable to be honest. @daviesgeek linked to a very similar question actually... – nohillside Aug 16 '13 at 6:49
  • I'm trying one more time (you're a tough bunch). That three year old question really doesn't do it. Some goof ball just added a copy and paste post full of marketing non-sense to the thread. Still no good. I'm looking for real anecdotal, up to date information. – plainclothes Aug 16 '13 at 15:01
  • There is no such thing as a "best" alternative valid for everybody and you got an impressive list of applications to try out already. I'm sure you find something for you among them. – nohillside Aug 16 '13 at 16:17

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