Well, I have an update. After removing engine again, checking the exhaust cover for leaks and resealing, I went back to checking ignition. While the spark on the lower cylinder seems to jump a sizable distance, one thing I hadn't tried is feeling the difference in the spark plug wires. Suffice it to say that the upper cylinder (that's running great) has a lot more 'bite' to it. Although you could feel the spark on the lower wire, it was a far cry less of a shock than the upper wire.
Which begs the question - with all new ignition parts (lower coil/condenser/points replaced twice), gap set, new metal core wires, etc....any idea what would be restricting the spark on the lower cylinder?