The more I experiment, the more I'm leaning towards the OEM solution. The only pipe/flange combo I ever had that didn't leak was an OEM flange with the split ring and the OEM seal.
I'll try a few things, and I'll even give one attempt at a high dollar o-rings like Kalrez (at $50 each, but they claim 50% higher temp rating than silicone). However, with all the other projects I have going at the moment, I can't promise when I'll get to it.