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If I'm right about this ... iTunes Match uploads files you already have and gives you back DRM free versions in a better quality?

and ...

Apple Music lets you download any file in iTunes library, but with DRM?

... I'm sure this won't be the case but, if you have both, do you get unlimited downloading of DRM-free music downloads from Apples library?

1

When using iTUnes Match you will be able to download a copy of your mp3 file (256 Kbps) from iTunes servers directly to your devices DRM-free.

If your file B.mp3 doesn't match any B.mp3 file on iTunes servers, then your file is uploaded to your iTunes Match account (same quality as local file) and it can be downloaded on other devices DRM-free.

Every file available on Apple Music has DRM, meaning: all the files you save for offline listening aren't DRM Free. Also, some files on Apple Music aren't available in every region.

Hope this helped!

EDIT

Corrected answer regarding the DRM state of iTunes Match files. Source.

Thanks to @fschoenm for correcting me!

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    This is not true (see support.apple.com/en-us/HT204962). Using iTunes Match will give you DRM-free music. – fschoenm Oct 6 '15 at 11:11
  • Thanks @fschoenm for the correction. I had assumed Apple would never let users download DRM free music like this, but apparently they do. This means that you can download illegitimate music files and then "laundry" them using iTunes Match. – dordio Oct 6 '15 at 15:19

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