You might be interested in Boris Trapsky, a Lichess bot that "estimate[s] your skill", then plays "interesting, tricky moves for you".
The sentiment above that "engines are built to find the highest win-rate moves" is wrong. Engines are built to find the "best" moves, with the enginemaker choosing the definition of best; it just so happens that most makers of engines are interested in "highest win-rate". The discussion above about only caring about the best move, not the second best, is not a fact of chess engines in general, it's only a fact of chess engines that use maximin.
This engine's goal is to give its opponent some swashbuckling fun, and I believe it uses the "find a move that's crushing against suboptimal responses" method you propose.