Kirk,
The engine should stop and start from any position, in either forwards or reverse, there are no dead spots designed on this engine at all. The only time it could fail to start is if running on steam, there might be a hydraulic lock caused by condensing water, or if on air or steam, whilst the engine is bedding in, internal frictions have to be overcome for the engine to start. Both mine tick over and run on 5 psi. But they have had a lot of running time. The last steam show I did, they got about 12 hours each spread over 2 days.
If the cranks are exactly 90 degrees to each other, and the timing is set at exactly 90 degrees lead to each crank, then there is always a power stroke, either up or down that will start the engine in motion.
Auto oil is much thicker, air tool oil is like 3 in 1 oil, and is really too thin for bedding an engine in. It will allow more friction to build up due to it having a much thinner film layer.
You are correct, yours is the fourth, but second if you exclude mine.
You definitely went the hard way, not only were you converting from metric to imperial, but you upped the scale as well.
Unfortunately, it will only have the same power or even less than the smaller one, as you kept the bore sizes the same as the smaller one, but increased the moving masses and friction by going larger.
But, you gained a lot of experience, that is the biggest plus about your build.
John