Windows – How to fix paths when iTunes truncated path names after adding music to a folder

iTunes keeps a lock file in the directory to see if there is an instance of iTunes running - only one is allowed at a time.

Similarly, if you're using the same directory, each version of iTunes will overwrite the library file, so trying to maintain two different sets of music within one tree isn't really possible. At least, that's what happened last time I tried this.

You're better off having Home Sharing enabled, and then having one Macbook at a time run iTunes pointing to the library.

The other can then use a blank dummy library, and play whatever the first is sharing through Home Sharing. Either can run in each role, just hold down Option at start-up to decide if you want to use.

Personally, given a family with a bunch of iPhones, AppleTVs, and laptops, I have a single iTunes server machine that is always on, with a very large library. All music is in my iTunes Match account, all videos can be synced over the air through home sharing, and wireless syncing. It's the closest I've found to an iTunes server device.

I would suggest a combination of your first and last ideas. You could re-add your Music folder to your library, and then use a script to change the location of the old entries (correct metadata) to the new entries (correct locations).

Pseudocode rough draft:

for every song in the XML file (seek)
  search the rest of the XML file for other songs of the same name
  if only one is found (found)
    log seek's name to file1
    if found is newer than seek
      copy found's Location value to seek
      remove found
    else
      copy seek's Location value to found
      remove seek
  else if more than one is found
    log seek's name to file2 (for manual editing)
  else (no others are found)
    log seek's name to file3

This script design would assuredly be quite inefficient, but it would fix most problems itself, and you would (er, should) only have to review the songs with more than 2 duplicate versions.

See this answer for details on how to make these XML changes take effect on your library.