It makes sense. But based on my years working with insurance it’s not going to work
I believe it is very much like healthcare insurance. And there’s a cap. So if the cap on policy one is $1000 day and the cap on policy two is $1200 when you submit your claim they want to know. what have you been reimbursed from other sources. So yiu write $1000 day from insurance one. At that point they’re going to give you $200 a day. Not another $1200, regardless of what you’re out of cost expenses were. If you don’t tell them that you were already expecting the other insurance and they find out everything is invalid and you won’t get paid anything
Honestly, this is a vacation I would consider moving to another time. If you can’t afford the cost to quarantine and there are no affordable alternatives anywhere around then this might not be the time to go where you’re planning to go
Have you spoken to the resort about this also? I say that because resorts in other parts of world have come up with some creative ways to handle this. I know of some that charge you a couple of hundred dollars for an insurance policy and if you test positive the insurance policy their kicks and they put you up someplace. they may have a plan that you might find more fordable than your insurance scheme