For better or worse, half way through realizing it was stupid, I've bought myself a massive collection that I don't "own" on iTunes. Technically, it is tied to my Apple account, but there isn't a way to transfer ownership, or etc outside of Apple even for e.g.if I die.

I think though there will be some laws passed hopefully that will allow us to own digital content outright in the near future, hopefully in a decentralized way.