Insurance? If you believe wingly's insurers aren't going to pay up even though they explicitly say they will, why would you believe any other insurance?
Really? I take it you've never had to make an insurance claim. Insurance companies are VERY good at finding reasons they shouldn't pay out, not to mention subrogation where they do pay out but then they try very hard to get the money off someone else.
If there's the slightest suspicion that you've been doing something outside the conditions of your policy, they won't pay up. I would read my policy, every word of it, VERY carefully before doing something like this.
Well, actually I wouldn't, because I flat out wouldn't do it in the first place, neither in FAA land, where for sure it is illegal, nor in CAA/EASA land, where it may or may not be legal, and we won't know until something bad happens and it really gets put to the test.