So now were on the right track, because you still need to get this figured out so then I know what to do with my rig as I have the exact same fault (stumble) and runtime hack fix (choke).

I'm not a fan of high(er) timing advance FWIW.
But I do have a bit of a different setup, that being the Offenhauser dual carb setup with two Carter WA1's and you have the single OEM SD40. I suspected too much air given my two carb setup, and the choke closes one of the carbs down air-wise (only have choke cable connected to one carb). But chocking also increases the throttle. Both of those factors impact the airflow through the carb and hence the fuel draw. My suspicion on too much air is linked to that event, transitioning from low speed circuit to high speed - possibly a bit also from idle to low speed. I've messed around a bit with lean drop tuning but haven't completely saucered and blown this so I'm not convinced I've traced that down. I've also sprayed everything to find a vacuum leak, and I've smoked out intake and exhaust system using a vacuum smoke checker thingy. And of course I've replaced the head casket, honed the cylinders and replaced rings with NOS OEM rings, cleaned up the valves and honed the seats and set the valve gaps, new dizzy at start of rebuild (less than 500 miles), check point gaps (but need to check dwell), set timing and idle speed, yadda yadda yadda. And I'm getting 14.5mpg which is pretty good IMO and there's no smoke anymore out the tail pipe. So I'm driving it

.
Hurry up though and figure this out, I'd like to eliminate my stumble.
Oh, and I'm not much help either.