If one were looking for ways to exert maximum load, individually, on insurance industries (car especially), I would suspect it'd make sense to think small scale damage, on many targets, generating as many small scale insurance claims as possible, while creating minimal possible jail time in the process.

Small scale destruction of property charges are extremely rarely punished with any severity - and in places which operate under principles of common law, you're essentially guaranteed a very short stay, at worst, if you are convicted of any such crimes. This allows you to maximize load on the insurance companies labour while minizing your down time.

In addition, submission of what can turn out to be frivolous claims, in such places as you might not be pursued criminally for doing so, can be a way to put additional load on the insurance infrastructure.

Insurance infrastructure tied up with that would have cascading effects on structurally dependent industries. It could seriously fuck things up for rich folks, I'd suspect.

Low personal risk, high impact.

Thoughts on this hypothetical, spotting anything I overlooked, got flat out wrong, etc?