Hope the right person sees this that has a definitive answer.
For a random state I picked, the Description of Coverage states:
"Benefits will be paid, up to the amount in the Schedule, for the forfeited, prepaid, non-refundable, non-refunded and unused published Payments that you paid for your Trip, if you are prevented from taking your Trip due to one of the following unforeseeable Covered Events that occur before departure on your Trip to you or your Traveling Companion, while your coverage is in effect under this Policy."
It reads that benefits are paid for "your Trip". Normally I'd interpret that to mean for each of the trips you may take in the covered year - and there is no mention that there is a maximum limit. Unfortunately, on one of the enrollment pages, it shows the following:
Voyager Plan
(max per plan)
And there it is -"Max per plan".
There's a chance you may get different responses as depending on where you live, policies and policy language (even though they're all from DAN) can be different. I can't even get an annual policy in my state.
Since none of this really helps, I'd suggest calling DAN for a definitive answer!!