Insure the Roof (wind/hail) in OK? Or just pay out of pocket?

[Ian Verzoni]

Wondering what the best strategy is.  Do I put a low deductible on my wind/hail and then use insurance to pay for a new roof once it fails?  I'm worried about how much penalty I'll have for using my insurance.

Or, do I save on monthly premium and hold a high deductible, and pay for a new roof out of pocket once it fails?  That way I don't get penalized for using the insurance.  I hold enough to cover a roof out of pocket if needed.

I appreciate what thoughts/insight/experience folks have had, thanks.