UPDATE -- success! in the comments below!
EDITED to note I am not trying to "double dip" and get vouchers and money back. Travel Guard agents instructed me to get the vouchers and indicate that the hotel and airline would not provide a refund, only vouchers, and that I was willing to forfeit the vouchers to Travel Guard in exchange for money back.
I contacted Travel Guard in June and filled out all of the many forms they sent me to obtain refunds for a prepaid nonrefundable hotel room and AirCanada tickets. We had purchased pre-existing medical condition insurance, and my travel partner is now scheduled for a total knee replacement at the time we would have traveled (so we weren't trying to get reimbursed due to COVID). Forms we returned to them included completed and signed medical forms claiming traveler could not travel, and we even threw in the hospital written confirmation of surgery date. Per their instructions, I sent copies of all original hotel and airline reservations, copies each entire email chain requesting money back and being informed only vouchers were available and copies of the credit card statements with the original billing information.
Today I got an email telling me that "As many refund policies are changing" I need to re-confirm that the airline and hotel won't refund my money and that the reconfirmations have to be as of the date of this request. This is absolutely absurd and clearly designed to get me to give up my claim. AirCanada hasn't suddenly decided to refund tickets. But there's no way I'm going to be able to get something in writing for them re-confirming my cancellation/voucher request....they are barely responding to normal email requests and a request to reconfirm something they've already put in writing isn't going to be answered. I was originally told it would take them at least 3 months to process my voucher, and my one attempt to contact them by phone led to almost 2 hours on hold. No one is going to email me to reconfirm what they already told me! Additionally, the hotel in Rome has already cancelled my reservation and issued me a voucher. Even without a language barrier, I doubt if they'd reply to a request to re-confirm this. Why would they when they've already confirmed it in writing?
What can I do to fight this? Travel Guard is being ridiculous. I sent them everything in writing. They have all the cancellation information, including the written statement from the hotel and airline that they are only giving vouchers. It's absolutely ridiculous that they say I need to get that information a second time, two months after I cancelled and obtained all the information. Is there anything I can do/anyone I can contact (or threaten to contact) to get them to drop this absurd requirement? Because I really don't think I'm going to be able to get the information a second time, dated as of today.
What especially ticks me off is that I'm talking about $2400 total claimed, a drop in the bucket for a company like travel guard, but a lot of money for me. We gave them all the medical paperwork and every document they requested and this is so nuts.
Thanks for your help and advice on this!