To summarize:
It did the same with points/condenser.
It did the same w/a W1 Carter and also w/a rebuilt Rcchester B.
You need to retard timing to start then advance to run smoothly.
It will not restart w/the timing advanced.
You are now indicating it runs better w/partial choke.
That is generally an indicator of the engine running lean and other than correcting the fuel/air volume via the adjust screw, you have a vacuum leak.....
How did you test for a vacuum leak?
I've used carb cleaner w/very good results but if/when I need to troubleshoot a vacuum leak again I'm going to try my handheld propane torch to see if it can detect easier/faster. If not carb cleaner.
If you can't locate a vacuum leak you might want to pull the intake manifold, check/clean and ensure the mateing surfaces are smooth, check all sides for cracks and put all new gaskets on it.
Set the timimg w/the BB on the pointer idling at 450-500 rpm.
I wouldn't worry w/setting via vacuum at this point. I would recommend road testing to test these settings and slightly retard via the octane adjust if it pings under load and/or advancing via the octane adjust if it hesitates badly after it's warmed up. Then try the warm restart.
My 49 w/a 216 and Rochester B starts very easily cold (w/choke) and 9 times out of 10 restarts just as easily with out choke when warm. It doesn't ping under load and pulls hills impressively for it's rated HP. All w/the timing set w/the BB on pointer at 450-500 rpm.
Good luck
Dave