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Yes, XLD works very nicely with iTunes organization--I still use iTunes for all my organization. There is a simple option in XLD preferences to copy all rips into iTunes, and XLD uses very the adequate Music Brainz, and FreeDB databases for album tagging info. I find XLD the ripping perfect complement to iTunes' good organization features. The only downside is sometimes I encounter a track (or rarely an entire CD) with some weird aliasing issue, even for a seemingly immaculate CD, that brings XLD rips to a painful crawl (hours for one track). Rarely I am forced to resort back to iTunes rips (with error correction) for a particularly difficult CD (XLD is practically brought to a halt after hours), but I am still wary of occasional glitches in iTunes rips. XLD is slow because it is so uncompromising in capturing a perfect rip. Overall I am very happy with XLD.
I've had much better luck with Max; it's far more stable and doesn't arbitrarily change preferences (and it hasn't crashed on me in years; it did a bit with a PPC Mac on OSX 10.4x). You are limited to the CDParanoia engine with Max but that's not a huge limitation. Also, when Max saves it's files in the backup directory you choose (it will also add them to the iTunes library at the same time), it saves them in an appropriately named folder, not just the raw file scattered in the directory.
Max is no longer maintained or updated, and it uses an old ripping engine.
fwiw, I always use an external drive for ripping. I have had occasional errors with internal drives but the LaCie drives I use are always solid.http://www.lacie.com/us/products/product.htm?pid=11171