People have tried to have insurance against speeding tickets in my part of the world (Scandinavia), and those have been deemed illegal and stopped from paying out. I would expect a GDPR insurance would end up getting the same treatment. I can't guarantee that this would happen in all of Europe, but I do expect it would.

When it comes to getting the max fine at first strike. The GDPR is not the first law in the EU with teeth. There are strict laws about corruption, pollution and antitrust here as well. Do companies get dinged with max penalty from the start violating these laws, not that I've seen. Why should enforcement of the GDPR be different from the current laws?