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Since this claim is covered by a garagekeepers (GKLL) liability policy, you have to see what the insuring agreement and other clauses have to say about paying for a loss.

The insuring agreement says that the insurer will pay all sums that the insured legally must pay as damages for loss to a customer's auto or the auto equipment. So, what the insurer will pay depends on what the insured is held legally liable for and in accordance with the language of the policy. As to what the insured is legally liable for, we cannot answer since that is a legal question. But, even if the insured is legally liable for everything that the customer lost, this does not mean there is coverage under the GKLL policy for everything claimed. The insuring agreement applies to loss to the customer's car and its equipment. And the policy defines a loss as direct and accidental loss and for GKLL purposes, any resulting loss of use.

This means that if the insured is held liable for the loss, the GKLL policy will pay for the loss of the car and the most that this will be, as noted in the limits of insurance clause, is the GKLL coverage limit of insurance shown in the declarations, minus the applicable deductible. So, you need to check the GKLL policy to see what limits the insured has; if he has a $25,000 limit, that is the most that the insurer will pay; if he has less than that amount, that is the limit that will be paid. And, losses are usually paid based on the actual cash value (ACV) at the time of loss. Unless the GKLL policy in this instance says something different, the insurer will pay for the lost van on an ACV basis up to the limit of GKLL insurance.

The GKLL insurer will pay for the loss of the van on an ACV basis up to the limit of GKLL insurance. However, the insurer will not pay for the deposit on a new car for the claimant since that is not a direct and accidental loss to a customer's auto. Loss under the GKLL coverage includes loss of use, so the insurer has to pay for loss of use, or car rental payments, for the customer, but these payments do not go on forever. The rental payments can possibly be limited by the policy language and you need to check that policy to see what it allows for loss of use payments; but, if no limits are shown, the amount is usually what is deemed necessary and reasonable. As for the personal items in the car at the time of loss, those are not covered by the GKLL policy. Coverage applies to loss to the auto or its equipment and not to personal items owned by the customer but having nothing to do with the auto itself.