Putting aside this weird concept of 'after-the-fact' licensing, where we infringe first, and then wait for the creator to negotiate what would make it all right...
Baio seems like a smart man, so it's easy for me to blame this current Internet culture being such that it didn't occur to him to ask about an iconic piece of artwork before reproducing it; can't assume 'fair use' is enough protection. And now we're too hung up on monetary values. Maisel asked for an amount - probably pulled out of his ass - that may have been significantly increased or reduced after a full trial. It may have turned out to be zero, and Maisel ordered to pay for Baio's legal defense. Or the opposite. We don't want Baio punished at all, which is understandable: he slipped, big time, and we're kinda certain he didn't do it with impugnity. But the courts, who would be closer to the facts than we will ever be, decide how much harm was done, and the amount it takes to compensate; we don't, as much as we like to act like we're experts on the negative effects of infringement. The litigants' personal incomes have no say over whatever amount is determined. So, settlement. I'm assuming Baio's still alive, still coherent, still makes a living, and now is a big fat crusader for fair use advocates. But no one has brought up the 'deterrence' aspect of this situation: what happened to him was sudden, serious, and affected his livelihood... that's entirely the reason it occurred to him to license the music. If there might be trouble, and you can't pay your way out, don't risk it. I wouldn't be the only one who doesn't think '8-bit style' is transformative enough, especially as the cover on a commercially sold product. If the subject was Floyd's "Dark Side of the Moon", would Baio be as ignorant about it? His examples of 'fair use' weren't very convincing, mostly because those were under very different situations, and he left out the all-important question of whether the creators of any of those original works were even made aware of these products, much less paid or compensated for them. He makes it sound like anyone could get trapped in a dark alley and attacked with a subpoena, but usually, if you don't do anything, you don't get accused of anything. Baio asked for a cover idea that won't land him in court. Is he kidding? There are a thousand things he could do. Do a faceless 'Miles & trumpet' sprite at 64x64 on a blue background: conveys the same 'message', and doesn't infringe on any photographs.