I wanted to verify TDC with the timing mark at 0, so shoved a borescope in cyl #1 and turned the engine by hand. It's dead on perfect.
"
IT'S dead-on perfect."
What "IT" are you talking about? Details matter! Is this regarding the alignment between the timing mark on the damper, and the timing indicator "0" marking?
Turned the key - it fired right up
Good sign.
About 5 minutes in, it started backfiring at WOT
Why on Earth are you whacking the throttle WFO during break-in?
Cherry red hot headers and that same wiring harness from before caught fire this time.
Refresh my memory about "that same wiring harness". WHERE is it? What does it control? How is it routed? Details matter, and I've read too many posts to remember the back-story on this engine.
How hot was the coolant temp?
I have header wrap and new wires on order.
You almost certainly don't need header-wrap. You need to make the damn thing RUN RIGHT.
When it runs right, the headers won't be that hot.
I'm also trying to convince myself to pull the trigger on the DUI distributor suggested earlier.
What's wrong with the distributor you have? If there's a problem, you need to fix or replace the thing. If not, you're wasting money on an already-over-budget project.
While I'm at it, I'm also going to have to order new wires for my Trans Am, because that's what I've been stealing the wires from lol.
There's a hundred electrical circuits in the engine compartment. What "wires" are you talking about? Is this regarding spark plug wires?
One last question here - Why is my timing mark always so far retarded at startup? I always have to twist the distributor CCW such that it seems I'm advancing the #1 wire all the way to the #8 cap terminal to get to 0° on the timing mark. This is with the timing wire on the firewall UNPLUGGED. Does that make sense to anyone?
No, that doesn't make sense. Time the engine per spec., and tighten the hold-down clamp properly. Re-check the timing AFTER you've tightened the clamp, to assure you haven't moved the distributor in the process of securing it.
If it changes from that point, you need to find out why. Something is WRONG. Clamp not tight enough, clamp is bent, hold-down-clamp bolt is too long, distributor is failing, distributor gears are wearing, timing chain/sprockets wearing, etc. Virtually everything that would wear to cause ignition timing changes, causes the timing to retard (not advance.)
Ignition timing with electronic distributors is almost--not quite--"Set For Life". Get it right when the engine is built, and it should stay in time more-or-less for the life of the engine, if you disregard potential failure of the various gears, chain, and sprockets that drive the distributor, and perhaps needing intake gaskets or some other service work that requires screwing-up the distributor position.