I went through this agony a year ago. Or maybe it was two years….. 900 CD’s ripped. It was a slow and painful process. If you are going to rip your collection, you might as well do it right the first time, get them on your hard drive, then you can screw them up at your leisure. Just make sure you keep the original rips somewhere that you can keep the folder unadulterated.

I would highly recommend you rip them to FLAC first. After trying several different programs, I sure wish I would have just used DB Poweramp first. It will rip to two different bit rates and dump them into two separate folders at the same time. You can set it up however you wish. Warning: be sure you have your options set up for tagging as you want them to be recognized the way YOU want them filed and not the software defaults first. If you don’t, you will forever be trying to fix them. Another plus for DBPoweramp is that it will grab album art as you rip. Many don’t, and it’s very, very difficult to find artwork after the fact unless you enjoy more pain to find each album one at a time. I’ve tried several batch gathering tools to find the art work, and none work. iTunes does, but it won’t share them with other programs……

So after you get them ripped, I would do as I did. Buy an HP smart media server and store all your music files on it. They are cheap now. I installed Squeeze Box onto the server and I use the Squeeze Box Duet to talk to my home stereo. I listen to the FLAC rips with the SB.

For my iPod, I have the 320K ripped songs that are in a separate folder. I point iTunes to that folder.

iTunes does not like to play with other programs, so you will always be wondering just what in the heck happened for one reason or another.

If you are interested in doing this, just let me know and I’ll go into more detail.