We'll every thing is ripped now and I can make a few recommendations:

 iTunes was a disaster for classical music. There is nothing wrong with the Apple lossless encoding (I would of preferred flac), but its the way it organises the files on the hard drive. iTunes uses the artist as the directory name within the 'iTunes Music' directory. This is fine for most CDs I imagine, unless like me you have a lot of classical music. The problem here is the inconsistency of the ID tags, especially in the artist tag. Some people use the composers name, some people use the performer. The worst aspect is a classical CD may contain several different performers, this results in your CD been ripped to several different directories making it impossible for the squeezebox to find.

To correct this I had to manually change the ID tags (Kid3 works great on the mac) and then copy them into to correct directory. This is a real pain in the arse.

A better ripper is needed and Vortexbox provides this. Its set up so that any CD placed in the optical drive is automatically ripped to flac. The ID tags may still need editing but at least everything is ripped to one location. The downside is the weedy processor on my Proliant server means it takes about 15 minutes to rip a CD.

Tags are a still problem with classical music. If you want the Squeezebox to find your music you must be consistant which means editing them. I plumped for using the composer as the artist and then the major piece as the album name, with the orchestra and conductor appended to this. I don't need to be so consistant with the album tag because the way I locate the music on the squeezebox is to search by artist.

My advice here would be to rip a few CDs at first to test your method. See how easy it is too locate you music on the Squeezebox. Don't do what I did and rip over a 100 in one go.