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The Desired End Result is to migrate the iTunes library from the source machine to the target machine.

iTunes Match was happy with all but two songs in the source machine's iTunes library, so all but those two songs are already migrated.

The outliers appear to be DRM'd.

Will Migration Assistant handle this? Can it deal with just copying two tracks? Would it be less headache just to:

  1. Burn the two tracks to CD on the source machine's built-in Superdrive.
  2. Mount the source machine's Superdrive from the target machine.
  3. Re-import the tracks.
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I believe the process you detailed in your question is the easiest way to do it.

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If only two tracks didn't get picked up by iTunes Match, any form of manual copying them will do

  • put them on an USB stick
  • establish a network link and copy the files directly
  • use AirDrop to copy them over
  • send them by mail
  • transfer them over via Dropbox
  • (or, if all else fails) burn them on a CD
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This guide might be useful. It doesn't save you from temporarily storing your files on an external device i.e. USB flash drive or CD, but you can "remove" the DRM tag.

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