I'm kind of like Alan. I do buy CDs and listen to vinyl often. For me, mp3s and even m4As with most codecs have been literally unlistenable. I just don't enjoy the music and can only listen for a short time. Or so I thought -- more on this in a moment.
However, I like the convenience of having music on hard disk and the cataloging features in iTunes.
I found something of a solution to the download conundrum that might be worth exploring for others, because it works for me. Well, actually, it's a combination of things that work for me.
First, I discovered HDTracks, a site where you can buy and download high-resolution music at significantly higher bandwidth and sample rates than CDs. Granted, the catalog is still relatively small, but there's enough there to make the site worthwhile from a lot of labels. For those into jazz, world, acoustic and classical music, it's almost a godsend, but even the rock and Americana stuff they have plays back with higher resolution than a CD, and you can run it in iTunes or other players.
HD Tracks automatically downloads the full album cover and liner notes along with the music, and you open it as a PDF and can not only read it, you can enlarge it. For an old guy like me, that's pretty nice, since CD liner notes are impossibly small for older eyes.
Second, I discovered playback software that uses different audio algorithms to play back both compressed and uncompressed formats. At first reading about them, I was skeptical, and didn't even want to bother. However, when I got into HDTracks, I found a few that were free trial downloads, so I decided WTF and tried several out.
Some of them sounded a little better than iTunes in terms of clarity, but also sounded a little phasey and weird. But I found one based on the Izotope audio engine that was created for mastering digital audio in the studio (and that I have used in the studio where it sounds damn good). It's called Amarra. The difference in sound quality with hi-res audio is easy to hear on good speakers, and it runs in conjunction with iTunes. So you can have all the iTunes features for cataloging and the store, and at the same time have a significantly higher quality listening experience.
Obviously, if you don't have good playback equipment, it's not worth bothering, but if you do, this is a good start at high end computer audio.
Amarra is Mac only, but there are equally good options for the PC that also are free test downloads (according to my creative partner, who uses PC). This stuff comes in a variety of price points. Amarra is under $200, and is absolutely worth it to me. Amarra's main competitor offers a solution for around $50, but I don't think it offers the same fidelity.
Finally, the best part is that for those of us who do find it necessary to download compressed audio for music we can't find elsewhere, mp3s played back on Amarra are actually listenable. They sound like cassettes in comparison to LPs, but I can listen to them for long periods now without having the urge to turn off the music. That's pretty nice.