Why not rip your CDs to ALAC which is Apple's version of FLAC? You get much smaller file sizes, about 5% of original, no data is lost, and all of your devices seem to work well with ALAC. I don't see where AIFF offers anything of value to you...
AIFF vs Apple Lossless Ripping
I have a large music collection that I have ripped using Apple Lossless and error correction turned on. I have recently seen several postings saying that AIFF (with error correction turned on)is the way to go. Would anyone care to address the superiority of AIFF vs Lossless, and if possible, explain why one would potentially be better than the other? And, if AIFF results in a larger file, approximately how much larger (percentage). I'm trying to decide if it's worthwhile to re-rip a 1400 cd collection.