I dunno, for me it is not about breaking rules, it is about actual outcome. If there is no game after all these years - this is shitty dev, even if there is people who loves tho eat shit. As for him being smart - don't think so. If he was smart, he'd completed the game and started another project. Or at least he could make separate chapters, which would made a whole project management several times easier. That way he could keep his milk farm AND have a good reputation of responsible developer. But he choose the dumb milk route. It is a one-way road now.It's probably very very very rare that a dev doesn't eventually fall prey to the almighty dollar one way or another. Sucks, but what can you do?
Ultimately, though, DC was smart enough to have a donation pool that's tied to 'doing something' and not specifically 'pay to get game', which is what I've argued in the past. He essentially takes advantage of people being easy to get to donate, and isn't specifically scamming them out of the game itself. Semantics, I suppose, but rules are made out of that. And can't get his ass if he isn't really breaking any rules.
"It's called a hustle." to quote a certain Disney movie.
His only possible outcoms:
1) losing patrons sooner or later, coz of they suddenly get +1 INT,
2) complete game years later and losing patrons coz of them not wanting to support another 10+ year project.
3) making super efforts to fix his reputation, for which he's got nor the smarts, nor the balls.