You buy or access a file on iTunes from one Apple device you own, it's available on EVERY Apple device you own. What are you blithering about "not portable?" You can also share that content you've purchased with your family using their AppleIDs. . . again, what do you mean "not portable?" All he'd have to do is buy it once and all of his AppleTVs would have the same content on each one.
So you are basically saying this "billionaire" relative is STEALING his content via torrents when it is totally unnecessary?
I was talking about this with an office mate yesterday. He uses iTunes and hates the non portability issue too. For him it is the need to play them on non-apple devices. He now just uses bit torrent for most stuff.