re: #381 Walter L. Newton

1) Which version of iTunes are you using? There is a verison 10 just released on Mac, probably on Windows as well. Also ensure your iPod touch is up to date as well.
2) Open Preferences and go to the advanced tab. Make sure “Keep iTunes Folder Organized” is checked. This, I know, is for music albums and tracks, but may also work for your case. If you wish, the folders can be arranged under your iTunes media folder - check the next box down if you wish.
3) Use File, Add to Library … to add your files to iTunes. Apple may allow you to drag & drop but it’s rather brain damaged about it.

Hope this helps. The iPod Touch can be a useful gaget if you can get it to work the way you work.