But it isn't like you don't get a benefit for "repurchasing". The DRM-Free versions are encoded in iTunes Plus, which is twice the bitrate of the original DRM-ed tracks. And the "repurchase" isn't really a repurchase anymore.
Since iTunes Match began, Apple discontinued the "30 cents per track" upgrade from DRMed 128k AAC to Un-DRMed 256k AAC, in favor of the $24.95/yr iTunes Match subscription.
But wait! There's a (good) catch! Once you subscribe to iTunes Match and Apple "replaces" your old, broken DRMed copies of songs with brand new NON-DRMed 256k versions, you can then DOWNLOAD those Tracks to your LOCAL Library. Those songs are then YOURS TO KEEP, even if you drop your iTunes Match subscription!
So, instead of 30 cents per song, what Apple now offers is essentially a $25 FLAT FEE to convert ALL of your DRMed tracks. If you only have a few, better to just repurchase those tracks; but if you have a number of the old iTunes DRMed tracks, $25 to convert them all isn't so bad. And you can either keep using iTunes Match at $25/yr, or simply DROP it, and have your nice DRM-FREE, iTunes Plus-Encoded, versions.
https://www.usatoday.com/story/tech/columnist/2015/01/18/itunes-drm/21964513/