If the songs are in the cloud that middle ground doesn't work.
The problem is games requiring "authentication servers" to do anything. The general thought has been when these servers were removed the last act of the company would be to release an update that disabled the requirement of the servers... however this has never really happened.
It frustrates me as thanks to tools like DosBox I am still playing games on my Mac that I first played years ago (Master of Orion 2 specifically). There is a distinct possibility that every game you purchase will no longer work in 5 years between DRM'd executable, proprietary platforms and authentication servers.