I had almost this exact situation this past summer. We had a VRBO reservation, my wife had an injury before the trip, and we had to cancel. It was still within the window to get most of the cost refunded from the owner, but there was a $200 cancellation fee. I made a claim on my Sapphire Reserve through Eclaims for the $200 and was successful on the first try.
Regarding the points you had trouble with, I found that a version of "not applicable" worked for flight info, but it had to be done in a particular way:
- Flight Number: type "NA"
- Departure Airport: type "N/A", wait for the popup menu to come up, select "N/A, Not Applicable, , "
- Arrival Airport: type "N/A", wait for the popup menu to come up, select "N/A, Not Applicable, , "
- Common Carrier: start typing "not applicable", e.g. "not"; when popup comes up, select "Not Applicable"
For travel booking vendor, do you mean the field labeled Travel Supplier that appears when you answer Yes to "Has a Formal Claim Been Filed Against the Travel Supplier?" If so, you are correct, VRBO is not in their list. My solution was to answer No to the formal claim question and ignore the red letters that say "A claim must be filed with your Travel Supplier". The form then allowed me to continue to the next page.
For medical paperwork, Eclaims wants their form ("Attending Physician Statement") filled out. I don't know if they would approve a claim without that form but with the other paperwork you have; I just know that I used their form as instructed and it worked. I filled out the form myself (typed using a PDF editor), brought it to my wife's followup appointment with the surgeon, and he was happy to sign it.
I attached the information they asked for and nothing more:
- monthly billing statements showing the VRBO charges (I edited the PDFs to highlight the charges)
- copy of cancellation policy for the reservation (a PDF of the rental agreement with the cancellation policy highlighted)
- for Travel Itinerary, I used the emailed receipt from the owner
- copy of emailed cancellation confirmation from the owner
- Attending Physician Statement form
Claim was approved in 33 days with no further documentation required.