Should I include the equivalent monetary “cost” of the airline ticket that I purchased with frequent flyer miles?

Generally the insurance companies will not insure tickets purchased with reward points or miles because no money has been paid. However, you should insure yourself for adequate trip interruption coverage. Make sure that you have purchased enough trip interruption coverage to cover the cost of an economy ticket home plus the cost of any unused, non-refundable land arrangements that you might lose if you have to interrupt your trip.