Regarding your #1 (or, alternatively, [A]), there's simply no reason to think that what worked for Trump in the Republican primaries--already a bit of a freak show selection of the electorate--will work in the general election.

No, Lewis was just 60 when he died. It's not written in the rules, at least not that I saw, but look at the list. Quine, the first winner, was already in his 80s. Putnam, the most recent winner, was in his 80s as well. The award is clearly slanted, as I note, towards "formal" work, with Rawls and Nagel being the exceptions. How seriously they take the 'formal' part (it is a prize in logic & philosophy) will no doubt affect how much longer they can aim for philosophers over the age of 70.