Earlier quoted context omitted.
I kind of doubt that matte_black's gamble (because that's what "insurance" is for costs which you could easily carry yourself if need be, unlike e.g. medical costs) would include that either. Then again, I'm surprised how many "insurances" cover things under your control (like dropping a device) so I might be wrong.
I would be 100% covered up to $500. I’d rather deal with a credit card company than a government anyway.
If the airline does you wrong, at that point the CAA takes it up on your behalf. CAA ~= FAA