If the gear is good, when the timing dots are aligned on the outer gear, the inner hub holes will allow access to the 3 bolts.
As the elastomer in the gear fails, the inner hub will drift backwards (CW), making it difficult/impossible to get a socket on the bolts when dots are aligned.
Earlier it was noted that the AFR was lean at idle, but if the idle vac is <14", then the AFR will be lean, as the low vac signal is not pulling much fuel out of the idle slot.
Since some smog stuff is currently disconnected, try the baseline non-smog setup:
Choke breaker gets connected to manifold vacuum (vac port on carb base).
Idle ignition timing should be 7-10*BTDC, vac hose disconnected, at 650RPM.
Vacuum advance gets connected to ported vacuum (carb base, valve cover side).
No vacuum goes to the Vac switching valve on fender.
Check the vac reading in the above baseline configuration, and test drive if it runs OK.
If the vac reading is still very low, then the engine is not pumping air efficiently at idle. Could be the cam timing is late, or could be the cam regrind is too radical for the engine, or...?