New IMac and squeezebox touch

As your using an Apple product you may as well rip in ALAC which is Apples lossless format.
You could choose another format either lossy or lossless when you rip but ALAC is open source and the Rega accepts it.
I would have the error correction tab ticked when you do the rips.

Rip to itunes then? I,presume the squeezebox server will access the iTunes library?

Personlly i would rip in FLAC to a suitable NAS. The PC. Has little to do with anything.

iTunes is the natural partner for Apple but others are available with Media Monkey being very popular and if you would like FLAC rips MM will do that for you. I use iTunes and have no problems, i also have iPods and as a whole its very easy to sync/use/enjoy.

Squeezebox and iTunes work fine and this may be worth looking through:

http://wiki.slimdevices.com/index.php/Beginners_Guide_To_iTunes

NAS?

 I said I was ripping to my iMac and isn't flac the same as apple lossless

A NAS (Network Attached Storage) will enable you to play songs without having to switch your iMac on.

Yes, both are lossless formats.

Unless you have a very good reason to use iTunes, I'd avoid. It's no great shakes in ripping CDs and the integration with Squeezebox (Logitech Media Server) could be broken in a trice by Apple releasing a new version. (They have no desire to help the competition, after all)

Many folks use XLD to rip to FLAC, which is a 'native' format for Squeezebox players (Apple Lossless would be transcoded to FLAC in realtime for playout)

If your discs are in mint condition, iTunes will produce bit perfect results (you can verify this by running the lossless files through cuetools on a windows computer). iTunes rips considerably faster, and is much easier to use, than any other ripper i have tried on OS X.