My experience the 2 times I had to use Chase rental insurance it is similar (my 2 data points are both in latin america, ecuador and brazil) At first they will bust your chops for all kinds of documents they know there is no chance you will be able to get. The main issue is the rental agency and repair shops have zero incentive to help you after they have billed your card to give you what you need, so in most cases, they will just ignore you.

The MO is just be polite to the agent that you have tried multiple times to get the information they are requesting, forwarding them proof via email. And explain you called over phone and cannot reach them.

After 2-3 back and forth they will send you your check. The main thing you need is the invoice of what they charged you, and of course photos of the damage.

I remember one time they even had one claims agent asking me for a list from the rental agency every single part that went into the repair, along with its cost. They're never going to give this to you. They will just give you an estimate of what they will think it will cost (of course vastly inflated), and then bill your card sometimes as late as 1-3 months later.

I've had similar experiences with insurance in general, they always play this little dance where they ask you for an insane amount of paperwork that they know you can't get, and after some back and forth they write you the check.