>I personally think there is a reasonable model of the world where customers explicitly pay a hundred dollar fee to have a highest-tier escalation to the office of the CEO/equivalent troubleshooting team and have them take a look at your case, but this is a model that has not yet been developed or in wide use anywhere.

This already exists in a sense. High net worth clients/well established business clients with long term relationships do get priority remediation and troubleshooting. The cost is just much higher than $100.