There is no easy way to do this! It is good that you keep your ripped CD's in a non-lossy format. Here's what I do...
1. Rip about 100 CD’s at a time to APE.
2. Select the cover art option to keep the cover art IN the file and a copy in the SAME directory.
3. Add cover art, lyrics, and any other tagging information that you require.
4. Select all the tracks, right click and Update Tags from Library
5. Right click again and Rename File based upon properties.
Now you have the originals sorted. At this point, I backup the originals. My files are kept in the structure, \\server\music\ape_1, ape_2 etc. (About 100 CD’s in each folder is an arbitrary number, but easy to work with.)
Then I copy the whole directory to make an exact replica. i.e. \\server\music\ape_1 copied to \\server\music\mp3_1
Next change libraries, for example from “Original” to “iPOD”. Then import the media from \\server\music\mp3_1. There are two reasons for this. First is that you can check the all the tagging information is actually in the file as opposed to in MC. Second, is that I have accidentally deleted original files in the conversion process before ( and that’s a pain ).
Now, select all the imported tracks, right click, Convert Format, send original to recycle bin and update database. Then sysc your iPod.
As far as your question about MP3 quality goes, you will find many different opinions… For what it’s worth, I have an iPods and an iShuffle. I use VBR Extreme on the iPod and 128kb for jogging.
nick