and no song database (like from a fresh install)
Path index file? So you are saying that new install already has this "path index file"? The ONLY thing I find in the data subdirectory is "Remove.Me". Even when that is removed, WinCab still doesn't create the database.
Try this:
Unzip a fresh copy of WinCab someplace.
Edit jukebox.ini and add a songpath AND change "UpdateIndex" to False.
Save jukebox.ini (also change it from read-only).
Run wincab.exe
Wincab will find all the songs and compare them to its non-existent database to see if they are in the database. It will then error out after checking all the songs. You can also get wincab to do this by renaming the "data" subdirectory to something else.