I think iTunes is a superbly designed product. You just don't understand what it is designed for. You think it is a media management system. In reality it is trojan malware designed to make people think their Windows PC is broken and switch to a Mac

If we're talking about listening on planes while drinking vodka, though, we really have to keep our perspective before insisting on 320kb AAC or FLAC. My biggest problem on a plane, Bose QC's or no, is dynamic contrast. Sure you can hear fortissimo just fine, bit pianissimo comes across as silence masked by engine drone. I'm pretty sure the last time I listened to Stravinsky on a plane - I thought the music had ended five minutes ago by the time it crashed back to life. Listening in the car isn't any better. I think high bitrate / lossless is great for sitting at home with a nice HiFi or a great set of earphones - but the devices in my travel arsenal are probably fine at 140kb.