The stock head gaskets aren't exactly a weak link, especially with l19 studs. If the surfaces were perfect and clean on assembly with adequate stud torque, they should be fine for high power use.
What do you have the studs torqued to?
Once a head gasket developes a leak it will get worse and worse and cause problems even at lower boost and eventually no boost. We had a head gasket go out on a 1725rwhp viper during a pass and it ended up melting down the block in the whole area!
Your gaskets leaking could be damage that occurred a while ago and it's just getting noticeable? Getting the ignition timing to do what you want it to do using the reflash is sort of difficult I have gathered. My car is always attempting to add more timing and runs much more aggressive in the cool air on the street that it did when I tuned it. I might fear how long term reliable this engine would be at the power I run if I was wasn't using e85... And not because of the engine itself but because of the ecu controlling it doing some goofy things at times.
I'm probably not telling you anything you don't already know... Just thinking aloud and brainstorming.
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