NOOB with a TIMING light gun

Yes. Really. Stock engines can deal with high initial timing because they have low cylinder pressure. That's why engines with high static compression need less initial timing.

It's perfectly normal to have total timing including vacuum in the 60* range at part throttle. Vacuum cans typically pull in around 20* or so.

Perfect example. My stone stock 351M Ford has 21* initial timing at idle. Starts just fine when hot. Has total initial + mechanical of 34*, PLUS whatever the vacuum can pulls in. Runs like a top. Lower compression engines NEED more timing.

Everyone seems to think high initial timing is a "hot rod motor" thing. It's not. A real hot rod motor with higher static compression needs less initial timing since it has higher static compression and higher cylinder pressure.

I'm sure we all speak from experience. "Stock" engines can actually have higher static compression since the "stock" cams are typically of less overlap etc... My 70 Cuda with the 440 +6 engine had an old school Crane 520 with split duration in the 292/282 area and pistons down in the hole about 0.050 with thick head gaskets. It liked 19 degrees initial but it was hard to start hot without the retard solenoid. It seems quite logical to me that the OP's stock 440 might have the same issue. This was also before the new starters were so plentiful but I did have the longest of the old school starters. You can easily have 19 degrees initial at Idle RPM with weak springs and still be less than that with the distributor at rest or a lower RPM than your normal idle. Many of the "ALL in at 2500-3000" crowd went overboard on the soft spring trend and had erratic timing at idle which was not really an issue on a drag car but can have drivability issues on a street car.