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I persevered and finally got iTunes Match to work.

After it uploaded a ton of songs, I created a playlist as suggested here and, over the next day or so, deleted and downloaded higher quality versions of my iTunes songs.

I'll eventually go through and weed out the duplicates. I've seen a few.

Will I renew in a year? I don't think so. Then again, having all of my songs available on my iPhone might just do it. This year it was a no-brainer. Next year, less so.P.S. What did I finally do to get it to work? I don't think this did anything, but I held the option key while I turned off iTunes Match (which apparently deletes the cache or something). Then I turned off home sharing. Then I turned iTunes Match back on, and started the process. I'd previously tried the "option" trick but not turning off Home Sharing. I've since turned it back on again.

P.P.S. It worked before, and yet, now on this same computer iTunes Match shows as off. I've turned it back on again and it's going through the process, albeit a bit more quickly. Why would it turn itself off? I'll add more in the comments if necessary.

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