Speaking on Monte Cook, I don't know what his old work was like, but his game Numenera was the big thing that truly brought me into tabletop gaming, and the larger cypher system games that have spawned from it also seem quite popular. At least their kickstarters do well. But they also tend to lean on an assumption of the players being good guys. And regarding Tyranny, it is indeed a brilliant rpg. But I also have only played in ways that are basically heroic. I think your general arguments about people's feelings on evil playthroughts, etc are correct.
Glad you found a game you like

I think he changed after 4e fell on its face - he left or was ousted for a while and he came back but he's very quiet nowadays. In 3e times his big issues were: 1) the ranger is OP 2) we have too many monsters than are too similar 3) evil needs to be supported and rewarded
The BOVD and The Return to the Temple of Elemental Evil were his big contributions. In RToEE you have 4 evil temples, each representing an evil element. The way to win is make a deal with one temple against another temple. If you are don't do that you only have one other, less than ideal, place to sleep. Each temple has a magic longsword connected to the evil altar. The winning strategy is make a deal, betray your erstwhile ally, rinse and repeat until you have no temples or just one. If you destroy the evil altar and save the village the swords are destroyed.
Good parties leave with no loot and no advantages - you have a diamond but you need to return that to the dwarves, the magic swords are gone, you don't get three wishes because you refused to free an evil god from its bonds and you didn't get any stat boosts because you didn't use the device that allows you to steal ability points from helpless enemies. The rewards were the friends you made along the way.
Evil parties get all the loot, status, stat boosts and the favor of an evil god.
Which was significantly more rewarding of evil than the original ToEE because the evil vs neutral dilemma in that module was: do I destroy the game breaking, god level evil artifact (and make the big bad evil easier to kill) or do I try and turn the artifact against the end boss and keep the evil powers for myself. Neutral was the ideal game play - you lied and cheated but the big bad dies in the end.