Major File Resolution Bug in iTunes

Question

I have repeatedly encountered what I consider a major problem iTunes has in resolving file names. Here's a recent problem that almost lost me a customer. I'm an audio engineer and I use iTune as an audio format converter. I had just finished an audiobook project spanning 6 CD's. It's in AIFF format. I wanted to send an MP3 version to my customer over FTP. I used iTunes for the conversion.
I cleared out my iTunes library, then dropped the original AIFF files for CD 1 into iTunes. I went into the import preferences and set iTunes up to create 128Kbps stereo MP3 files. I then selected all the files and started the conversion. This worked fine for CD 1.
After saving these MP3 files outside iTunes, I deleted all files from my library. I then dropped in the AIFF files for CD 2 and started a conversion of these new files. The files for each CD are named in the same manner: "Track x.aiff" where x is the track number.
Here's where the problem occurred. iTunes totally confused the first set of files from CD 1 with the new files from CD 2. Even though I had deleted the old CD 1 files, somehow iTunes still pointed to the originals or maybe the ones in the trash. When I did the MP3 conversion, I got CD 1 files, not CD 2.
To make sure this wasn't a mistake on my part, I repeated this several times on two different Mac's (a 1.25 GHz G4 iBook and a 2.0 GHz dual G5 workstation), both running Mac OS 10.4.8. I got the same problem in all attempts.
Bottom line, iTune has a real problem with two files of the same name and will likely get them confused.

Answer 1

Why didn't you import them as Disc 1 thru 6 of 6?
And why didn't you give them real file names?
I thought doing them one CD at a time would be less likely to confused iTunes.
The track names were generated automatically by an audio editing program I use. In fact, they were originally named like: "CD x Track y.aiff" When I first inported them into iTunes, it stripped off the "CD x" portion of the name.
After saving these MP3 files outside iTunes, I
deleted all files from my library.
How did you save them outside iTunes?
Select them in iTunes, then drag and drop into a folder.
And how did you delete them from the libary?
Select all, hit the delete button on the keyboard and then confirm that I want to move them to the trash.,
As an aside, why did you use 128 kbps?
If it's just speech (no music), you could use 32
mono/64 k stereo and the quality would be just fine.
It's mostly speech but there is some music. I wanted a little better quality that 32/64.