Will multiple life insurances policies pay off when the policy holder dies?

Yes. Why not? Most insurance companies will check to see if any additional insurance policies exists for a policy holders. If so, they make sure that only one policy pays off. This is especially true (for example) if you are covered by two different life insurance policies one as part of your automobile insurance and another as a straight term insurance policy. In the event that one policy pays off in full the other policy is prorated by the other so that the beneficiary doesn't receive the full payout amount for the second ploicy. I've never heard of this in life insurance, I'd like to see some documentation on that. Sure, it happens in medical insurance, not life.