Ailing engine (Updated after teardown)

I think people worry about the surface finish requirements too much. Especially on a deck surface that is not freshly machined.
One of those things you hear a lot from people who haven't tried it themselves... I asked my machinist (experienced race engine builder) if I needed to deck my 5.9 Magnum block to work with Cometics. He said not to worry about it, factory finish is fine. Engine has been together with ARP studs for 7 years and at least 10k miles, zero leaks. I don't think Cometics are really necessary though considering OP has iron heads and boost level is pretty moderate.

I agree with @Newbomb Turk, your total timing is too much; not that far off from a hot NA SBM. That gasket should have held up fine if it wasn't detonating. It should have boost timing retard or at the very least take out a few degrees with the current setup. I also bet your rod bearings are showing copper. The head bolts probably loosened up over time from the heads being lifted with the detonation.

Just because it lasted this long before something broke doesn't mean it was running perfectly... It is a Mopar after all, they got the beef to handle abuse.