I think there is a business opportunity to setup a company selling internet rights corporations. As an end user, you purchase a corporation, and this business takes care of all the paperwork, etc. Then, when you as a partial or full owner of the business want to download an iTune, you ask the president of the business (you) to DL the iTune and make it available to you (the sole beneficiary). When you die, the corporation - and all of the rights it has to digital music, videos, etc. - can be passed on to your heirs.
F' Apple and F' the RIAA and MPAA. The skirt the gray areas of the law every single day, and even go so far as to lobby Congress to enact contradictory legislation such as the DMCA, and then they think they can tell us what we can do with material we have licensed? Nice try, but no.