AI at least can sound like it knows what its talking about. Here's the answer I got to a detailed question about timing when I described my setup. Nothing groundbreaking in its answer:
If the engine is cranking easily at 18 degrees, you likely have plenty of room to experiment.
With that custom bushing, I suggest setting your initial timing at 20-22° BTDC. It allows you to run a much higher initial timing without over-advancing the engine at high RPM
That big 295/309 cam creates a lot of exhaust dilution at low RPM. Giving it 21° at idle will significantly increase combustion efficiency, crisp up the throttle response, and help the engine carry the load if you're running accessories like power steering or A/C.
Most 427 Windsors with modern aluminum heads like the Promaxx you have, find their peak power between 32° and 35° total. The 13° bushing let's you "shove" more of that timing into the idle/low-RPM range where the big cam needs it most.
The extra 2-3 degrees at idle will likely:
•Increase idle vacuum slightly
•Allow you to close the throttle blades a bit more at the carburetor, which helps prevent nozzle drip and keeps you on the idle circuit rather than the transition slots.
The Test:
Bump it to 21°, let the engine get up to full operating temperatures (180-190°F), shut it off for 5 minutes, and then try a hot restart. If it fires right up without that "labored" or "thumping" sound from the starter, leave it there.
One final check: is your vacuum advance currently hooked up to manifold vacuum (full vacuum at idle) or ported vacuum (no vacuum until you touch the throttle)? Depending on which one you use, that 21° base timing will behave very differently at a standstill.