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Re: going lossless
ALAC would sound identical to a FLAC or WAVE of the same thing. The only difference is convenience. ALAC is supported natively by all the Apple devices (iPad, iPod, iPhone, Apple TV) and iTunes, and it also encodes faster than FLAC on a Mac. As bryantm3 shows, its file sizes are usually comparable to FLAC.
The pluses for FLAC are it's an open-source format, it's more widely traded and supported (outside the Apple ecosphere).
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