Spoofed in the late 1980s in Scott McCloud's Destroy!!, which consisted of nothing but one-frame pages depicting a battle between two superhumans which effectively totals the city around them.
In the comic book series The Boys, a CIA subdivision is set up to take superheroes to task for the damages they incur. One character's girlfriend was graphically killed in front of him by a speedster throwing another superhuman into her, right after they traded "I love yous" for the first time. Of course, The Boys is, depending on who you ask, a deconstruction or just one long bitchfest about superheroes in general. While heroes in other genres might at least make token attempts to minimize property damage or justify it with equal contributions, the superpowered jerkasses of The Boys just don't care and would slaughter a million civilians to apprehend a jaywalker.
There was an amateur comic in Svenska Serier where villain and a Designated Hero, both musclebound bricks, bust out against each other at a high-class party, tearing the place up in the process. The destruction soon rises to ludicrous levels until they suddenly call it off and don their civilian disguises. The manager of the party at the introduction, now the only apparent survivor who is sobbing on his knees in the midst of the destruction, is then approached by two surprisingly muscular suits who inform him that the insurance policy they provide would be excellent should something like this happen again.
In Miracleman, the title character tosses a car at the villainous Kid Miracleman in a futile attempt to stop him. Recalling the battle, Miracleman says that his defenders claim the car was empty. "I'm sorry, but that simply isn't true." Even worse, it wasn't a car. It was a school bus full of children.
The "superhero kids" comic PS238 tries to handle the social consequences of superpowers realistically, and has brought up the concept of the "Super Samaritan Laws," which were lobbied for and passed to give superheroes some legal protections from the occasionally destructive consequences of super fights, considering the fact that if they didn't intervene, worse damage would likely happen. It helps that, in the PS238 'verse, many supers have gone into private and public work that doesn't involve crimefighting, and the MegaCorp Clay Industries (founded by a metahuman super-intellect) is explicitly mentioned at one point to create 'instant-buildings' used to rapidly re-build urban areas damaged by superhero battles.
In the Luna brothers' The Sword, the collateral damages of Dara Brighton's battles with Zakros and Demetrios are treated realistically: the public at large reacts as if the world is ending.
The Mighty Magnor hangs a giant lampshade on the trope. The two comic book writers who accidentally unleashed Magnor are on the hook for his ever-increasing property damages—balanced only by the ever-increasing licensing fees offered by Hollywood agents.
Averted in the Don RosaScrooge McDuck story "The Cowboy Captain of Cutty Sark". While selling bulls to the sultan of Djokja during his cattle days, Scrooge is forced to retrieve said longhorns from thieves, and the resulting destruction, including 'a Scottish cowboy steaming into a port on a run-aground ship', is so costly that he's forced to give up every penny from his sale.
Averted in Robert Kirkman's Invincible several times. Fairly early in the series, a duel between Invincible and Omni-Man shatters entire skyscrapers, killing thousands — so even when Invincible manages a Pyrrhic Victory, he can never reveal his secret identity for fear of criminal charges or even assassination attempts against his family. The trope is averted several times later in the series as well. You'd think that a guy who publicly saved the Earth from annihilation multiple times would be forgiven when a moment's hesitation results in a city being vaporized... but that's not how humans think.
One issue Go Go Power Rangers has Zack spending his Spring Break doing volunteer work for a senator trying to pass a reform bill that would make the shamelessly apathetic insurance companies cover the damages caused by Rita Repulsa's monster attacks and the Power Rangers' battles against them.
Used by Starscream as part of his plan in The Transformers: Combiner Wars. He secretly sent Menasor to attack the colony of Caminus, then sent his troops and Superion to "rescue" the colony (and having two Kaiju sized robots fighting caused plenty of collateral damage) and offered aid in rebuilding as a way to manipulate them into swearing allegiance to him. Windblade said it was obvious what Starscream was trying to do, but the alternative was a slow death as the colony's Energon reserves gave out.
Often tackled in Empowered, as superhero fights cause a lot of collateral damage that is only made worse by how reckless many heroes are (on one occasion Major Havoc nearly killed the girl he came to rescue).
Most notable are two of Emp's three times using Car Fu: the first time she (ineffectively) throws a car at a rampaging monster only to see the old man owning the car looking at the remains of the vehicle, and the other time, as she uses the various parts of some cars as scaringly effective weapons, we're treated to flashbacks of her time in college, where she mentions that if a superhero has to use as weapon the car of people who struggle to pay their bills the less they owe the owner is to make the most of their sacrifice. She also mentions that car insurance rates in superhuman-populates cities are five times the national average specifically because superheroes continue throwing them at their foes.
