I have had clients who had a second hail claim two years after the first. The client had pocketed the money after they had sent the check to the lienholder for endorsement. After the second hail claim the client sent the check to the mortgage company for endorsement. The mortgage company held the check and told my client he would need to open a trust account where the funds could only be dispersed to the licensed contractor who had a signed contract to repair the roof.
Here's the fun part. Since insurance had already paid for the roof once and the insured had not repaired it, the second claim pay out was much smaller. It was $3500 short of what was needed to repair the roof. Since the insured had already spend the funds from the first claim, and the deductible had been applied a second time (separate losses mean separate deductibles) he had to come up with $5500 to get the contractor to get the funds for the repair to the roof.

