... even with iTunes volume cranked all the way up (even with SoundCheck on), it can barely achieve even half the decibels when the original is streamed through AO ...
Try without Sound Check; that's probably what makes it sound different. Also, make sure you aren't using "Sound Enhancer" or the equalizer in iTunes -- those would
definitely change the sound.
Wow, patents, you say? Still, what of AIFF? Are there patent issues with that as well?
There is zero difference between what you'd hear with AIFF and WAV. They're both storing uncompressed audio data; AIFF just does so in big-endian (PPC) and with slightly more sensible headers. With WAV export already implemented, I see no reason to switch to AIFF.
I just export as WAV and use iTunes or Max to convert to Apple Lossless. You could just as easily convert to MP3 this way if you'd like. My only misgiving with this method is that I have to redo all the tag information manually, but it's really not that big of a problem.