My iPods have died and are now extinct so I can no longer listed to my original iTunes format purchases. There was a was to upgrade older downloads to the $1.29 license version to allow me to listen on non-apple devices.
Windows, Windows 10
Old school iTunes purchases (2009 or older) in 128K AAC protected format can be burned from an authorized computer to audio CD and then ripped back to the computer as unprotected files. As noted, the scheme to upgraded these to iTunes Plus as it was once called no longer exists. It may still be possible to use a subscription to iTunes Match, which in the past has allowed these tracks to be matched in the store, after which you may remove the (current) downloads and redownload in 256K DRM free AAC format, which you can continue to use after closing the iTunes Match subscription.
tt2
Old school iTunes purchases (2009 or older) in 128K AAC protected format can be burned from an authorized computer to audio CD and then ripped back to the computer as unprotected files. As noted, the scheme to upgraded these to iTunes Plus as it was once called no longer exists. It may still be possible to use a subscription to iTunes Match, which in the past has allowed these tracks to be matched in the store, after which you may remove the (current) downloads and redownload in 256K DRM free AAC format, which you can continue to use after closing the iTunes Match subscription.
tt2
I believe that option is long gone.
upgrading older iTunes format songs to the multi-platform versions
