I've heard album cover art works really well if you buy from iTunes. I've also heard that on average there are 22 tracks purchased from iTunes on the average iPod. Which means most people have to rely on iTunes to download artwork automatically for them. But it works badly. Very badly.
I don't have numbers (numbers are boring anyway), but my experience is that automatic downloading only works about half the time. So if I have 600 CDs, I have to go out and find ~300 covers. If it takes 1 minute per cover, that's way too much time. And heaven forbid you library gets corrupted and you have to go through it all again. It's so broken there are various utilities out there to download artwork for you. I just googled "download artwork for itunes" and got 170K results (admittedly not all utilities).
Now why is this so hard? The mp3 files are tagged with artist and album name as well as all the track lengths. I rip my CDs and get the information from a CDDB database. (These aren't illegally downloaded files with weird tags.) And Apple has iTunes, so Apple has all the information about the CDs. Is it really so hard to match this stuff up? No, it's not. There's no reason this hasn't been fixed.
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