And the answer is...

The Triumph issue became apparent as soon as I pulled the points cover off the magneto and the points fell out into my hand. Looks like the points center screw worked its way out and/or destroyed it's thread. Then the points started working itself out of the taper, wiggling, and destroyed the woodruff key. This is the 3rd magneto failure and I think I have less than 200 miles on this bike. FUCK!

If just the points plate was damaged it would be an easy fix, unfortunately the threaded insert inside the armature is destroyed too, so the whole thing needs to come out.

As for the compression issue, I'm not sure. I'm getting 150 now on compression. Not sure if the oil hasn't leaked out yet or I had a leak in the tester. I'll keep an eye out. In the meantime, I once again need to pull off the mag. Old bikes are getting old.