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I, too, have pondered this. I think but do not know that an insurance company would want to see cash out of pocket for valuing the loss. By that, I think they would need to see the initial expenditure. And if it is points, I fear they would not see that as an expenditure. I do try to be careful to use credit cards with travel insurance to pay the associated fees for the award booking.
What I have purchased is medical evacuation insurance. It is an annual policy. We go to some remote corners of the world. If we are in an accident, I want to be returned to my home town for care. A friend had a severe heart issue while at the company office in Delhi. It cost the company $500K to medically evacuate her and bring her to the US. I'm happy to pay my $300 policy and hope I never need to use it to avoid that kind of financial risk.
I have booked this for international travel for some of the medical/other travel benefits (we have 2 kids). I do realize that most of these benefits are duplicative of some credit card coverage. Generally most things we book with points our refundable (e.g. Hotels, Southwest, etc.) - so I generally plan that I can cancel. For other flights (e.g. AA/United/Delta) - I assume they would cover the cancellation fee (so if I spend 60K Points and there's a $200 Cancellation Fee) - I would assume I would get reimbursed for $800 ($200 tickets x4). I would assume there is no cash value for the 60K Points at all.