Originally Posted by zen100

The whole reason skiplagging exists at all - is because airlines are exploiting monopoly power in certain routes, charging some customers more than others based upon the starting point - almost always because there is more/less competition. People should be careful very about skiplagging, but certainly shouldn't feel any moral guilt about it, given the airlines behaviour.

To answer to the OP's question, I have claimed insurance on an exEU trip .They did query it, but I was able to show positioning flights/hotels and they paid out in full. In my case, there was no skiplagging, so that was one difference.