Your problem is you miss the difference between his valuations for insurance purposes and lending purposes.
In the 80's I held some rental properties. So, I know a bit about this.
Probably not as much as you, but I did depend on an advisor for some financial purposes. At that time, I could buy insurance for rebuild cost (which may have been higher than assessed value and/or taxable value) or for a sum lower than either appraised value or rebuild cost. The only thing I could not do was to insure at a lower value than an outstanding loan on the property, per the loan agreement.
I have not done an analysis of Trump's business tax returns, so, perhaps you could explain to me what fraud Trump may have committed.
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