Before I can make that calculation, we need to know how much annual premiums are for a house like below valued at $375,000. 1%, 2%, 5% deductible premium costs will be needed and I don't have that info. How much did you save by going to the higher deductible?First, there is no 'average' price of a roof. It's like asking you what is the 'average' price of a house. We need more details.
So, let's use this as an example:

2800 square feet of living space per Zillow. House built in 1999.
Several things to note on this. We have single story and two story roof requirements. We have porches front and back requiring special attention to low slope techniques, and we have pitches that add to the cost.

The price of this roof will come in around $18,000. This is for a good quality Class 3 architectural shingle with modern synthetic underlayment, and accounting for low slope materials to satisfy install requirements, replace all accessories and flash accordingly.
Deductible on this one is $7500. Based on what I know about this neighborhood, that is a 2% deductible.
So....
Deductibles on a house valued at $375,000:
1% = $3750
2% = $7500
5% = $18,750
Most people I roof, based on their premium, have paid for their roof many times over. Think about that. You have sent enough money to your carrier to reroof your own house several times. You can bet your sweet tail that when lightning hits my home or hail destroys something, I am claiming that every single day of the week and I will max that claim out to recoup my costs.
What you need to think about is how much MORE you are paying every year to keep that 1% or even 2% deductible, how many times you have roofed your house due to age or storm damage, and see if it makes sense.
For me, on that house, I would keep a 5% deductible if I could swing it. That would be the minimum. If I could get a higher percent deductible, I would absolutely do it. I can eat an $18,000 roof without noticing it and if I have saved that much from the reduced deductible every 5 years, then you've saved it anyway and that makes sense.
When you get insurance coverage, make SURE your house is properly appraised. Can the customer above rebuild that house for $375,000? I don't know, maybe, but it might be close or undervalued. Then, don't insure so your deductible is cheap and you can get a roof covered. Insure your house as high as possible that you can afford in case the whole thing is catastrophically destroyed or you have a seriously large repair. Figure your odds, don't let fear and emotion work into the equation. I would go for a 5% deductible on the house above if I could. I am plenty comfortable covering that, and if I SAVED the money I would have spent on the 1% deductible, then I have paid for my own roof anyway.
The house above has the original roof. In 26 years of insurance coverage and premium payments, not once was a roof claim made. ****CAVEAT****Some carriers are requiring re-roofs at 10 years for asphalt shingles. Not all, but some. This seems to bother people a lot, and it should as you may not need a roof at 10 years. However, if we use the math above, bullcrap insurance policies ignored, you've saved enough to cover that yourself still.