the hypothetical person would be in breach of Contract with the Apple Music TOS already:
- You may not tamper with or circumvent any security technology included with the Services.
Removing the DRM, even with a purchased program, is tampering security technology included with the services
The Apple Music ToS does say though also:
- You may burn an audio playlist to CD for listening purposes up to seven times (this limitation does not apply to DRM-free Content).
So, you would be allowed to create a CD during your contract time, and then you would be allowed to turn the CD into mp3 with a tool useable for that. You do not tamper with the DRM or security technology on the i-tunes-file as i-tunes itself (and the contract!) directly allows to create a CD.
Turning the CD into mp3s afterward is not circumnavigating the DRM as the CDs can't have copy protection that interferes with the legal use of a CD - in fact besides a "do not copy me" flag a CD may not contain any copy protection or it is not a CD by its Red-Book Standard. Including the XTC and MediaMax copy protections to prevent such did bring Sony BGM into huge legal trouble in the 2005.