So a couple months ago I undertook the task of going through my CD collection of ~500 and ripping the ones which were not already in my iTunes library. This amounted to about half of them. I choose to rip at 160kbps. This seems like a good compromise between size, for the iPhone, and quality, for the hi-fi if I were to play them thusly. Oh and make sure you rip as MP3, you don’t want any DRM in case you decide to port your stuff somewhere else.
My dvd-rom drive ripped through them at about 42x, so each one only took 1-2 minutes. I also went through and attached album cover art for the ones which iTunes wasn’t able to find on its own.
This process was somewhat laborious, yet satisfying. I was going to pursue one of the apparently many software solutions for accomplishing the cover art attachment, but I ended up just doing it manually. Let me offer some tips.
1. iTunes is able to conjure and adhere a large number of covers for you on its own, assuming you’ve utilized the CDDB for naming. So your first move is have it pour through your collection via the following option. It should apply album art for any albums you’ve ripped which happen to be purchasable in the iTunes store:

2. Moving forward, you’ll want iTunes to be attaching album art for you as you rip new CDs, when possible. Set that up via this option. (Note this setting is on the General tab in versions prior to 8.0):

3. Now the meat of your task. You’ve got to go through your coverflow basically, and see which albums don’t have art attached. Then you’ve got to obtain it. I choose Amazon.com. You find the album there, then click “See larger image”. Sometimes there are a few versions of it, find your favorite, some are worse/smaller than others. Save the image in a folder on your desktop. Now to attach the image.
Align your iTunes window on the left of your screen. Align your folder with the artwork on the right, and display it as thumbnails. Highlight all the songs of the album. Right click your selected songs and select “Get Info”. Drag the icon into the artwork box. Press ok. Done!

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