As noted above, my family member whose Hertz rental was stolen had the whole thing covered by Chase without any issue whatsoever a couple years ago. It was pretty awesome.

But I'm still trying to get my issue with Hertz and Card Benefit Services resolved. Note that with Hertz, there IS some room for negotiation. But they'll only go so far (I've managed to narrow the CBS/Hertz bid/ask spread from an initial 30% to under 5% of the total claim).

It seems you're much better off totaling your rental or having it stolen than having it merely damaged. If it's totaled or stolen, CBS can't refuse to pay diminished value or Hawaiian shipping costs. Stupid incentive system.