I think you might have misunderstood what I'm trying to achieve.. While I didn't explicitly say so, I do actually need to keep everything on the root of the drive, one of the radios I play music from doesn't allow shuffle if the files are in sub-folders. Hence my query regarding the file naming.
If i create a playlist, I want the synced files to have the following output style, regardless of what album track number each song meta tag has set:
* 001 - <artist> - <title>
* 002 - <artist> - <title>
* 003 - <artist> - <title>
* 004 - <artist> - <title>
* ...
The incrementing number doesn't necessarily need to be padded, but I could do that with MM, so it would be nice... But I don't see how placing the files in subfolders help me here?