Physical media was once subject to the restriction (grey area) that it could not legally be re-sold in the US. Then, through series of court cases and legislative changes (laws), it became possible. The First Sale doctrine.
In the EU, one can sell one's digital files -- in particular, software -- even if one does not own anything physical. This is regardless of what EULA the user clicked through to purchase a game, for example, on Valve.
I'm looking for help with something less extreme -- simply making it possible to inherit one's parents' movie collection. Or we could just say to the grandkids, sorry, Harry Potter died along with Grandpa last week.
It would be great to see Apple take the lead here, and do the right thing for families of the deceased, without needing to go through a long court battle and legislative process to move towards the EU model.