iTunes 10 file directory organization in Windows I'm pretty new to iTunes.

I have a video series that I want it to be imported to iTunes and be organized in this hierarchy:

Artist->DVD No. and Title->Lesson No. and Title

The files are now organized using Windows 7 Tags \ File system.

Example:

D:\My Videos\John Due\Learning about Birds\4 - The Wings\2 - Advantages
If you want to use iTunes to manage your media files, it's best to stop bothering about file system structure for these media files and just let iTunes do its magic. Any specific sorting and selecting can then be done directly in iTunes (at least after you updated all the metadata).

In your case I would probably import all the files and then use playlists and playlist folders inside iTunes to get the structure I want: