MRY
Wormwood Studios
(1) Even assuming the $40k is true (which suggests he overpaid by a lot), he's talking specifically about Queen's Wish, where he redid the art from scratch. That suggests he probably paid something like $40k total on art for all his prior games combined, which just recycled the same art.Here he uses an example where out of $200,000, he (and his wife maybe, he says "we") takes home $100,000. As you said, some of that money might be going back to him in some other form, but he is claiming that he pays out about $40,000 for the art alone.
(2) The $60k "for business expenses and insurance" largely means stuff for his home and his family: "between the salaries for the creators, the costs for freelancers to makes graphics, general business expenses for the year (insurance, internet, a new computer or two), and the printing costs for hint books, Geneforge 4 cost about $120K to make. ... I work for a salary...." Whenever I hear indie dev small business types talk about it, they describe a totally different experience from someone getting a W-2. Normal person gets paid say $50k, government takes $15k, he spend the $35k on his apartment, insurance, computer, internet. He gets paid $50k, he spends the $50k on his "home office, business insurance, business technology" and reports no profits, doesn't pay taxes. It's not quite that "clean," but that's why he's talking about things like internet as an "expense" rather than as a product/service.