So the Allianz claims guy called and told me that they would be okay with whatever Aeroplan told me to do. So I called AP and she told me to cancel for $90 and get my taxes and fees refunded. Then rebook for more than 22 days out then cancel immediately for $90 and then claim the $180 + tax and the insurance will be okay with that even though it sounds like it shouldn't be. It took the AP agent 30 minutes to do all that and I had to pay $203.40 but I had a refund of the $160 tax part right away. Then I claimed the $203.40 plus the regular ticket I had also purchased. So in the end, those of you who told me to rebook and cancel were right (at least I think so) and I can confirm the correctness of your advice in terms of the rules of AP. The AP agent said the rules are what they are and the insurance company knows about them and agrees to pay. That may be it.