Hi Andrew,

No problem; that’s why we’re here.

Unfortunately, no.  The loss incurred by lossy encoding is permanent.  You will 
have to re-rip those CDs.  This incidentally highlights another obvious benefit 
of lossless formats: archival.  When the next format-de-jour comes along, or if 
you simply find that you need higher quality encodes, a lossless format costs 
you nothing in ripping time, only conversion.

iTunes Match supports a maximum of 256Kb AAC; anything beyond that is 
automatically downgraded to 256 Kb AAC.  If you use iTunes Match, therefore, 
never download tracks to a device where you have lossless files, only copy or 
sync them across.  Before the 128 GB iPhone, this was my only option for 
getting access to all my music; now, all my tracks fit on my iPhone in 256 Kb 
AAC, so I no longer need or want iTunes Match.

It depends on what equipment you have and how much music you have, but I 
generally find that maintaining lossless files on my computer provides the best 
indoor experience both on speakers (computer or hi-fi) while AAC provides good 
enough performance while out of doors.  AirPort Express always streams using 
Apple Lossless, so if you have speakers using AirPlay, that means you get full 
benefit from Apple Lossless.  On an iPhone, where space needs to be saved, 
iTunes has the option of converting files as they are synced across, which you 
can find under the Summary section.  Set that up to convert to 256 Kb AAC and 
you can maintain a library of lossless files which sync across to a manageable 
size on your iPhone.  With most travel headphones, you probably can’t tell.

Good luck on your ripping project. :)

Cheers,
Sabahattin

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