My experience copying iTunes music Mac -> PC

Posted:
in iPod + iTunes + AppleTV edited January 2014
Besides the fact that our IT guy told me leaving a VPN connection running from my house all day was a no-no, it didn't work for streaming music from my home iTunes library to my PC at work anyway.



So, I decided to settle for copying music files from my PowerBook to my office PC. I've got a little over 16 GB of music at this point, and only 12 GB free on my PC, so I had to be selective. I decided I'd go for all of the unprotected music in my playlist "The Big Shuffle", a little over 3 gigabytes of music that I like to use with shuffle play.



I hoped it would be as simple as this:
  1. Mount my PC share, create an empty iTunes folder.

  2. Sort "The Big Shuffle" by Kind, then select everything but the Protected AAC files, which sort to the bottom.

  3. Drag the selected songs to the new PC iTunes folder.

Step 3 is where things fell apart. There were long pauses and spinning rainbow vortices of death (or at least vortices of delay), but then nothing would happen. No error messages, but no songs copied either.



Apparently if anything goes wrong, nothing happens at all, so there weren't any easy clues from where the copying stopped. By copying a few files at a time, and trying copies via the Finder that gave this misleading error message:

Quote:

The operation cannot be completed because one or more required items cannot be found.

(Error code -43).



...I finally figured out two key problems:
  1. Folder structure isn't preserved. All files copied by dragging songs out of iTunes land at the same folder level. This much didn't surprise me. The complication of putting all the files together at the same level that I hadn't thought about, however, was files with the same name from different albums. For example, God.m4a by Tori Amos, and God.m4a by April's Motel Room. Instead of trying to rename one of these files, iTunes simply gives up silently on all copying rather than try to put two files with the same name in the same folder.

  2. Some characters in file names block copying (even if Windows allows those characters in file names). I wasn't surprised that bullet characters didn't work. (I use bullets where I've joined two songs into one file.) The equals sign didn't work ("Let X=X" by Laurie Anderson) either. Nor would question marks ("Would I Lie to You?" by Eurythmics).

My solution?
  1. Sort songs by Title and look for all duplicate song titles. Temporarily add an underscore to the end of one duplicate to give it a different file name.

  2. Type troublesome characters that I know I've used, like = and • into the Search field, and in the matching songs that come up, replace those characters withing underscores.

  3. Copy files 100 at a time rather than all 570 at once, just in case I missed any trouble spots.

  4. When all the copying is done, type _ into the Search field, bringing up the list of altered song title, then restoring to their original state.

These characters were trouble: ? • =      (and probably a lot more I didn't run into would cause trouble too.)

These characters worked okay: & ( ) , . _ ' ! -

I guessed that ° would be bad without even trying it. ("99.9F°" by Suzanne Vega.)



Once the copying was done and I'd fixed my altered Mac song titles, I switched over to my PC and dragged the whole pile of 570 files into Windows iTunes. To my chagrin, for about 90 seconds iTunes CPU usage hit nearly 100%, and iTunes wouldn't repaint or respond. Perhaps performance on something other than an old 850 MHz Dell Inspiron struggling under the burden of XP wouldn't have been so taxing, but I'd like to have seen iTunes be a bit better behaved than this. Finally a progress dialog appeared, grayed-out versions of all songs were listed, and over the next few minutes the grayed-out titles went black as songs were copied out of the flat folder into iTunes own artist/album folder hierarchy.



I typed _ into the Search field again, fixed up the titles on the PC side, deleted the files from the flat folder (don't do this if you haven't chosen the iTunes preference that automatically copies files you drag in, instead of just pointing to them where they are) and I was finally ready to roll.
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