We purchased Travel Guard Insurance for a once in a lifetime 6 month trip. The last 4 month I spend many hours on the phone with Travel Guard Insurance, so far not 1 claim has been paid. They took away my online access so I am forced to communicate via email and phone only. They demand the same information over and over ( for example information about our US health insurance / Medicare) which I provided several times via email. In average I did spend about 2 to 3 hours per week dealing with Travel Guard unsuccessfully.
Now they combined several unrelated claims under a new claim number to confuse the matter even more.
They are asking for documentation that is not available in all countries. Not every country can provide the electronic receipt Travel Guard demands. There are still countries where you have to pay cash and receive a paper receipt. So if you feel like fighting with an insurance company for month Travel Guard is the right insurance for you, but if you want a reliable, reputable insurance do not use Travel Guard.
I had a very good experience with Travel Guard when I injured my knee on a Rick Steves Tour of South England in 2023. Obviously they require receipts and I had paper receipts for many expenses and I took photos and emailed them to TG. They were super helpful getting me home on a Delta Business Class ticket which they paid for in advance. It did take time when I got home to write up the incident and obtain a letter from the Rick Steves organization stating how many tour days I missed. I was reimbursed for everything. I had zero medical expenses because I was diagnosed in a National Health. hospital in Exeter. Medicare was not involved in my case, I don't know how that compares with your situation.
Thankfully, we've only had a couple of claims over the years for medical stuff. In all cases they did require documentation, but nothing unreasonable. Got checks within a couple of weeks of filing both times.
Why don't you file a complaint with your state insurance commissioner? They are going to have the leverage to hopefully get your issues resolved.