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The big bore master is making the pedal uncomfortably stiff but the system seems to finally work.

Any comments on why the small bore master didn't work? Bad master? Should I try a different master?

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Sucess! (1) You'd think bad master but I'm not grasping how it was high and tight with the one (offending) side blocked off but spongy with it hookup up then a diff master made both front sides firm as you'd logically think there was still air in the bad side (2) To confirm (or deny) I'd get a diff one with a smaller bore and bleed it out since you're getting to be a bleeding pro and can do it in no time and the smaller bore will get the pedal feel where it is more comfortable for you