Does my deductible apply on an annual basis or is it per claim?

The deductible applies per claim. For example, if your deductible is $2,500 and you have a payable claim June 1, you would incur the cost of the deductible. If you had a second payable claim on July 1, you would again incur the cost of the deductible. Each time you have a claim you incur the deductible.