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I don't think he submitted the claim. Certainly it will cover document replacement, electronics may be excluded. I understand the room was burglarized, but the LW should have had the electronic devices in the safe. That may have been burglarized as well, but at least that extra step will make an insurance claim easier and for that reason alone, it is worth it.
As an FYI, I am not familiar with Courtyard, but I have utilized the hotel safe in the lobby several times. It is very secure. Yoy have to key in to a special safety deposit box room, etc.
I asked this earlier but I will try again. What did the Detective assigned to this about the status of the investigation? I guarantee it will not be difficult to get a pilot's license, etc theft escalated through law enforcement. I imagine you would be in touch with the Detective weekly.
It is not likely that a homeowners policy will cover his items as they are for his business. This is why he should have had business insurance. He can submit claim to them, if he has it.
My BIL had his van covered by his pauto insurance. Not sure if they ever asked him if he used it for business. If they did, he probably answered no, as at the time he did not. He started using it for a small business he had with one client, a bank, wherein he visited the branches and performed maintenance duties and fix it jobs. His van was stolen in Miami, from a motel parking lot. His auto insurance did not pay as it was not stolen from his home and he was in Miami doing business. All his work tools were gone and the Van had been stripped. Even the seats, tires and wheels were gone when they found it.
Pilot license numbers used to be your SSN! At least the FAA *finally* changed that after years of pressure. @Jason E Jacobs can be a bit thankful he doesn't have that adding to his headaches! I hope he returns to update us...understand the nature of his job may make him incommunicado for days at a time.