When initially starting and not knowing if it's in time or not I get it as close as I can (TDC, points open, rotor points to #1). Then while cranking the engine and with the clamp on the distributor loose turn the whole thing one way and then the other, somewhere in there it will fire and run, then adjust timing by ear and lock it.
Once running you can set it any which way you please, be it a vacuum gauge, ear, or timing light.
On a first start you will probably choke it some, and no throttle other than by hand/foot as necessary to keep it running (when starting never use the throttle cable on the dash).
You'll need to judge if you've choked it to much or not and try not to flood it.
Check oil pressure immediately on startup, shut it off if you don't see any in 5 or 8 seconds or so after starting.
Grigg