(there may be many issues with this. therefore this may be a very ambitious enhancement)
If it is possible to create an iTunes plug-in that would couple this application with the internal resources of iTunes.
Changes to the files through this application would trigger iTunes to change the file within its internal database in order to keep playlists and what not in sync. (Must be careful if iTunes manages the file locations)
Possibly utilize (or import) iTunes' internal database/XML for extra information within this application
Work with iTunes Match
Work with iTunes' mechanism for retrieving artwork
(there may be many issues with this. therefore this may be a very ambitious enhancement) If it is possible to create an iTunes plug-in that would couple this application with the internal resources of iTunes.