A recent upgrade to the iTunes Producer software used by studios to encode tracks for iTMS distribution may be a good sign for the discriminating audiophile community, as Apple has included the necessary tools to create lossless AAC content that could presumably be uploaded to the online store.
If this happens, then great. The poor audio quality has always been one of my complaints regarding the service. However, if Lossless was to ever happen, there is no doubt that there would be a premium price. At that point, it just makes more sense (or cents) to go out and buy an album you to do what you please with. I’m skeptical, but looking forward to seeing if anything actually progresses.