Any idea what changed, if anything? Court decisions made in the meantime simplifying things?
Hopefully the content fits in a few buckets (cartoons, fiction, non-fiction) as far as different terms for rights might go. And then from there, you can lop off anything that's past its copyright term (?). Then maybe the next step is grouping works by the agent/publisher, if any? Or maybe all the contracts with the New Yorker are signed by individuals, with the New Yorker as a publisher. I don't know.