The most obvious case that comes to mind for me right now is a multi-chapter fanfic from years ago that I never finished. This included both a love triangle and an antagonistic, hate-to-love type romance, all wrapped up together. And this was at a time when I had an even stronger aversion to both than I do now. And these were the central threads of the plot, not some supporting B-plot. More recently -- I even wrote a DW post about it -- I was writing a nation of inhuman people as analogues of a real cultural group (my own, but still), which is a thing I've strenuously objected to in the past.
And now there's my Yuri Jam game, if it gets off its feet. When I was coming up with the concept, I was mainly thinking about a cutesy idea of "mad scientists", a kind of character trope that has lost all credibility to the point where it's automatically camp and humorous, in a self-aware way. At least in theory. It's impossible, however, for me to ignore the underlying creepiness of the story, even if I'm trying to tell it from a point of view that places value judgments on the protagonist's choices, and even f the game is built in such a way that it locks the player out of making any truly outrageous character choices. I have to find a way to write around and through it, and address it head-on while still allowing the game to be a little funny.
And I find myself wondering how it is that I keep finding so many corners to paint myself into.