Poorjohn
Liability insurance for aircraft accidents is mandatory. You cannot fly without insurance. It is mandated by Warsaw/MC99 and is a requirement of air services agreements.
Insurance against Regulation 261 compensation claims is not available on the market. Even if it was the premiums would be so expensive that no company could afford them.
I certainly hope no pilot would ever take the cost of compensation claims into account when determining if it is safe to depart. But as the courts have decided that just about any delay, baring weather, invokes compensation I fear that this will become a factor.
And how long will it be until the courts decide that the weather is also 'not extraordinary'?