In my case, all my sound quality comparisons have been with CDP's e.g. Meridian, Ah!, etc. My assumptin about iTunes is that it is a multi-media (audio and video) SW player designed for the masses; it is primarily tuned for compressed media. I want a dedicated music only foundation. Pure Music, Amara, et al, are designed with one purpose only, music reproduction. However, iTunes a an excellent media library management tool.
Recently, I took my Wyred 4 Sound DAC-2, MacBook Pro and external HD full of lossless media to a buddy's house. We spent the next six hours in a music fest evaluating and just having fun listening to all sorts of music, everything from standard Rebook to 24/192KHz. It was an ear-opener for my friend to hear what computer audio could provide, so much so, that the next week he ordered a bunch of new audio toys!
We listemed and compared CDs, the equivalent hi-rez versions, as well as upsampled versions (via Pure Music). Much of the CD equivalent hi-rez material is often remastered, so sadly, it's not a direct comparison. But heck, even 44.1 material sounds excellent on the Wyred 4 Sound DAC-2! Media mastered in hi-rez just sounds superb! There are no worries that there might be something lacking, since it's as close to the master as it's gong to get. The new SW playback possible with the likes of Pure Music means that we are as close to the master as we can possibly get, without sitting in the same room as the likes of Bob Katz, and other audio engineers.
Not only is sound quality at a new pinacle using Pure Music (and other's), but the ability to instantly, and randomly cue music tracks is a godsend. I use my silver (and gold) CDs to rip to the hard disk (using XLD). If I ever revert to disc-based playback, it will be for the black, oil-based vinyl variety, amongst other reasons, partly for nostalgic reasons. Although, to attain a similar level of fidelity possible even with CD Redbook playback, you'd have to spend litereally thousands more than the equivalent SW solutions!