Hello! I have a 1950 late model 8N (side mount distributor) and was having difficulty starting up this spring - problem ended up being a weak/old battery. In the process of diagnosing the issue, I also decided to give the ignition system and timing a bit of attention as it hasn't been looked at in a while. When I reassembled the distributor and cranked the starter - nothing happened for a few seconds and then a loud "pop" from the exhaust - which I took to mean the timing was way off. I compared my "before" photo of the distributor wiring to the results of my tweaking, and noticed that the wire that the distributor rotor was pointing to when the flywheel was at the 4 degree BTDC mark was for the cyl 2 in the original picture, as opposed to cyl 1 as I had just set it. I flipped the wiring back to the original positions and it fired right up.

So my question is thus: is it possible to have the flywheel installed incorrectly in such a way that the timing marks don't line up with cyl 1?

I had the clutch replaced and the flywheel machined at a shop a few years back and I'm wondering if they put it back on 90 degrees out of alignment.

Either you or someone before you had the distributer out and did not index the gears properly when they put it back in.
Put your thumb over #1 spark plug hole and by hand, roll the engine over till you feel it begin to make pressure. Then look into the timing hole as you continue rolling it over till you see the mark on the flywheel come up to TDC.
Then pull the distributer out and index it so the #1 mark on the dist cap is correct.
Easy peasy.

Thanks Ultradog!

I'm likely not explaining this well. When I was setting the timing initially, I did as you've described above. Felt pressure in cyl 1, rolled the flywheel over until the timing mark came up to TDC (set it at 4o BTDC per the manual). I then made note of the position of the rotor in the distributor and plugged in the spark plug wires accordingly - CCW 1-2-4-3, with #1 in the position of the rotor. I didn't have/make a mark on the cap.

When I cranked the starter, it fired on the exhaust stroke.

When I reviewed the images I took of the wiring before pulling the wires off, the current position of the rotor (when the flywheel is at 4o BTDC) was pointing to the spark plug wire for cyl 2.

I plugged the wires in based on the original orientation, and it fired right up, which would lead me to conclude that the timing marks are in line with cyl 2 as opposed to cyl 1.

I've attached an image to indicate what I'm trying to describe. Not sure if that helps.

My grandpa used to say “you thought you were wrong (in this case it would be “thought you were right”) but you were only mistaken.