Why do I keep blowing head gaskets?

Alcohol has better resistance to detonation than gasoline too, so that's not an equal comparison. It's very likely that in those instances, alcohol is the determining factor for not blowing gaskets.
That just furthers my point. The ethanol has a much higher latent heat of vaporization which does more than just the benefit of the higher octane. The E85 is only like 105ish, but the fact that it pulls so much heat out of the charge when it vaporizes really helps the chamber temps. But (my real point) the gen3 hemis in those circumstances are sealing up the chambers and not kicking out gaskets with very high cylinder pressures, so it’s not a mechanical sealing issue.