I buy almost all of my stuff from iTunes, so no lossless here. I also mostly use EarPods and my car stereo -- the speakers are nice now, but the head unit is still about 7 watts of factory tinnage. So it makes zero sense to even think about using anything like that. Heck, I downconvert to 128k because 16GB feels like 1GB.
I'd appreciate seeing Apple offer some higher-quality music along the lines of DTS audio. I'm not sure of the technical specifics of it, but I remember being blown away by DTS quality on DVDs in the 1990s. We're still using just 2 channels on most music audio.
This wouldn't help much with earbuds, but it would help when streaming to Apple TV or to a car system if it was a good quality one. Plus I'm sure the music companies would love to sell some upcharged music like the movie studios love charging an extra $5 for HD movies.