Here I am trying to set up iTunes. I want to add my 2500+ songs to my iTunes library. Since I’m computer savvy, I go to “file” “add folder to library” and select the directory — “my music” — where my music resides.
iTunes was able to find 864 songs. That’s a 34% success rate. Let me tell you how happy I am about this.
Bravo apple. Bravo.
PS - I opted not to sell the iPod I won since it had been engraved and personalized (kinda) on the back.

If you burn the rest on a CD, then in turn upload the CD to iTunes, it’ll probably transfer the rest. I know, it’s a giant pain in the ass, but that was the only way I found to do it.
Thanks Trickey, but I found another workaround. I just cut all the files from “my music” of the “my documents” variety and pasted them into “c:\my music\” and it worked.