So, if I'm understanding correctly, you used the insurance payment you received for your 2018 hail damage to repair the roof in 2019, after a natural disaster occurred.
Regardless, only the amount not covered by your insurance would be deductible. I'm doubtful that the IRS would take issue with you using your insurance deductible that you paid in 2019 as a deduction for the 2019 natural disaster. Technically, you're talking about two different events, which is what makes it so confusing.
If you ever were questioned by the IRS, you'd need to show evidence of the claim and the repair work. Obviously, the IRS could disallow the claim if you were ever audited (not likely). Keep in mind, however, that your insurance deductible would need to be an itemized deduction on Schedule A. If you're not itemizing your deductions, as many taxpayers no longer do, the entire issue is a moot point.
*** I am NOT a tax expert. I am a seasoned TurboTax user, and volunteer to provide assistance to TT users. Nothing I post is to be considered TAX ADVICE; I bear no legal liability for responses.***
