Well, are you ready?
The timing was off.
After a compression test (approx 150psi across the board) and a visual valve and ignition inspection, I was left with nothing obvious. I was prepared to go into the cam and timing chain. My Dad wasn't buying those as faulty parts and suggested timing it.
We set a vacume of 19, then set the timing with a light at 14° and took it for a spin. All is well.
I'm clueless as to why it started coughing the way it did. The dizzy hadn't come loose and the ignition parts are still the same. I'm not sure why the timing was off.
We didn't advance it as much as I like and it feel a bit slow, but at least it's running and not coughing or backfiring at all. I put about 100 miles on it without a hiccup.
Thank you so much for all your suggestions, help, and offers.