NOOB with a TIMING light gun

Everybody seems to be caught up telling him to set total timing. That's not the correct way. Set initial timing FIRST, then look at total. If total needs adjusting, then do it. Usually on stock distributors, you set initial around 18-20 or so and limit total to 34-36. Nobody's said any of that here.

Really? 18-20 initial on a stock 440? And it starts hot without hitting against the starter? Several people did mention a range of 34-36. I don't see where anyone said to "set" timing with the vacuum hooked up but to "check" it or see what it is just to make sure you don't melt it down at cruise. If with the vacuum connected and at 3000 RPM you get more than say 45 degrees there is potential for overheating or detonation when accelerating from cruise. Depending on which vacuum can your distributor is equipped with there can be easy or not so easy ways to limit the vacuum advance. Depending on how weak the springs are that hold the advance weights initial can be all over the place.