Check out Max. It is freeware and is IMHO the best ripping software for OSX. It uses cdparanoia to control the ripping process. Max can convert to over 20+ formats including all Apple formats. BTW, there is nothing wrong with iTunes as a player interface. I am exeremely paranoid when it comes to my ripping software.
Ckorody is correct. Use Apple Lossless format for your collection. It will save you space on your HD (about half the space of AIFF or WAV) without losing any quality. It has been said before but, depending upon the size of your collection, be sure to backup your music HD (I would use an external FW for the main music drive and another FW HD, tape or DVD for backup). Nothing is forever but there are precautions you can take so you won't need to rerip your CDs.
Computer to DAC is now. Enjoy your new setup!