I am fine with trademark protection, but you can't say that everything sold under a trademark constitutes the trademark itself. As for this...

I was just listening to an NPR segment on how Elvis Presley's image has become tainted by cheap crap, and that inspired Frank Sinatra to ensure the same doesn't happen to him. His biggest fear was that his face would be sold on a coffee mug. Should anyone be able to do anything with Frank Sinatra's likeness now that he's passed?

I favor a 'longer of (alternatives)' term that can persist beyond death, so if you finish your great work of art and drop dead the following day it doesn't become public domain as soon as you hit the ground, but that post mortem copyright should not last very long - maybe 20 or 25 years, the typical length of a human generation, and thus enough to support a newborn heir to adulthood, for example.

Elvis' image is only 'tainted' to the extent that the availability of cheap crap makes it more difficult to sell premium-priced crap exploiting the same image. I'm old enough to remember reading of his death in the newspaper and while I'm well aware of the existence of tacky Elvis products none of them reduce my enjoyment of an Elvis musical or movie performance if I'm feeling nostalgic. Elvis is as great as he ever was, you just can't charge as much for stuff with his name on it as you used to.

Sure, I understand Frank Sinatra not wanting to end up as the commercial equivalent of a punchline, nobody would. But let's be realistic here, his estate is licensing his recordings and likeness to sell whisky right now, so why should they enjoy a legal subsidy to operate a Cult of Frank Sinatra?

Should the estate of George Lucas be able to create new Star Wars movies in X years to compete with Disney's Star Wars movies in effort to undo everything they added to the universe "Because it wasn't George's vision", even though he sold off the rights?

Of course, yes. Would we be better off culturally speaking if people had to get a Shakespeare license before staging one of his plays, to ensure that no theater goers ever had to endure a shitty Shakespeare experience? Of course not.

I don't think brands and the products put out under then should enjoy legal protection in perpetuity, and for that matter I'm not sure corporations should either. In wills and trust/contract law, there's a 'rule against perpetuities' because giving people the power to set conditions that last forever just doesn't work out well in practice and so individual autonomy is sacrificed on the altar of the larger social good. When we apply property interest to immaterial things like texts or legal bodies, they should in some way reflect that which they imitate; just as a corporation is a legal embodiment of a collective human action - ie we treat it as a person for administrative simplicity - intellectual property is the legal instantiation of private human knowledge and that privacy should not be so strongly protected as to exceed human discretionary capacity.

Put another way, persons involved in a commercial negotiation centered around an exchange of information for consideration has the option to reject inadequate offers, withdraw from negotiations, and keep the valuable information to themselves until such time as a better offer appears or the value of the information expires. We grant a property right in certain kinds of information because of the considerable costs of creation relative to the tiny costs of reproduction, and I believe there is a sound economic and moral basis for doing so - but that basis must be rooted in some cognizable measure of individual human experience, which after all is the only sort of experience we can honestly lay claim to. Collective organizations may well have experience (in the sense that an ant colony may be capable of cognition, experience, and consciousness notwithstanding the limited mental capacity of individual ants) but the threshold of eusocial consciousness remains obscure and may be formally undecidable using existing methods. Insofar as legal rights and responsibilities accrue to individual humans, the median individual human experience must therefore remain our legal yardstick for the time being.