Red Faction: Guerilla had physics based modeling of damage to structures and an auxiliary game mode where the objective was to collapse as many buildings as possible within a time limit using demolition charges and other weapons. (Of course, the player is a noble revolutionary fighting an oppressive government so there's a fig-leaf of social acceptability.) Precise and quick placement of demolition charges on structural supports was key to getting a good score. If they'd had some sort of procedural map generation for it, I'd probably still be playing it today.