I can't get itunes to acknowledge that I need to redownload a DRM-FREE version of the music I already paid for.

What it says in the subject line. I have a huge number of songs that I'm just now realizing are "Protected AAC audio files," which is a load of complete crock, but whatever. I've tried following the incredibly convoluted and asinine directions about deleting the DRM version first, then going to the itunes store and clicking on purchased songs and re-downloading each one, individually, by hand. This is an unbelievably stupid and time-wasting method, but if it worked, I'd only be moderately peeved.
However, it doesn't work. Itunes refuses to acknowledge that the DRM version is no longer on my computer; as far as they're concerned, it's downloaded, so there's no way to redownload the non-protected version. Never mind that I've now been scammed into signing up for that stupid Match program, which I fully intend to discontinue as soon as I resolve this idiocy - apparently ITunes just flat-out doesn't have the ability to tell which songs they should just automatically replace because DRM is no longer a thing.
If the solution is obvious and I'm missing it, I'd be really happy to hear it - reply to this and mock me for not getting the issue. That's totally cool! But please don't tell me that I'm going to have to literally re-purchase almost 2K songs just because Apple can't do its job.

Have you tried using the Applications DVD that came with your MBP. It will work just fine. It CAME with your computer it is yours to use on that computer.
Give it a try.

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