It seems to me that the best user facing way to do this, is to export a playlist as CSV. You can do this pretty easily by going to a view that shows everything, like Audio > Files. Then doing File > Export Playlist . Select CSV. It might be easier if you limit the view to showing only a few columns that will help you. Something like the filename and maybe album, artist, and song name?
There are check boxes for whether to include all fields, or just the ones that are showing on screen.
Speaking of the Files view: Files has a Location column, which should contain all of your drives. You can isolate what you export (as a CSV) by selecting a drive. Select the files you want (highlight them) and then do an export playlist and choose "selected" instead of "all".
This might help you isolate your issue if you feel like it is on a certain drive or a certain path or something.
This isn't the easiest process nor the most automatic. I noticed that when I did a test, I got a lot of extraneous lines that said something like "<Item Name>" with almost nothing else on the line. I quickly eliminated them in my editor. You should definitely review the output of the CSV playlist so you know what you're dealing with.
Best of luck to you,
Brian.