So, I solved the mystery of the crazy advanced "initial" timing. Worn out distributor springs! I was getting ~ 10 degrees of mechanical advance even at idle. I am assuming at some point the initial timing was set around 12° btdc, but as the springs wore out, more and more mechanical advance crept in.
I wasn't pinging, because the total advance was still between 38 and 40°. A little high, but not catastrophically so. I assume I didn't have starting problemschool because the starter was not spinning the engine fast enough to get significant mechanical advance, it wasn't until it started running in its own that it reached that point.
After I got the distribute freed up and "initial" timing set to 12° btdc, I noticed a drop in high rpm power, likely due to the fact that I had unknowingly decreased my total advance to ~25°.
I put on a set of the P925D advance springs after realizing that my springs may be shot. Initial advance dropped right down to 0°, confirming that my old springs has given up the ghost. I now have initial timing set to 10° btdc, with total mechanical advance of 35° coming in right around 2800 rpm.
I still have the sudden WOT bog, but at least I have the timing and ignition all sorted so now I can focus on the carb.
Mycoses, the new balance seems correct. I have verified TDC, and verified with a protractor that the counter balance weight is at least in the same position as that of the old damper. Keep in mind, the old damper counterbalance wound not have spun, as it is not on the outer ring with the timing marks. The engine seems to run very smoothly now. The damper I got was from an Australian company, specifically designed for the Cleveland. Australia had the Cleveland in production for a much longer time than we did here in the US. That is part of the reason I went with that specific damper.
