I too an mechanically literate, but I'm not an engine mechanic. That said, I'm inclined to agree with you about positioning the #1 wire over where the rotor is pointing. HOWEVER, you always need to think of the next guy, or yourself if you have a poor memory (like me). That's why there's a "standard". If you're absolutely certain (measure three times, cut once) that you're engine is at #1 TDC compression stroke. I'd install the distributor in the position that the factory installs it. Then put the plug wires in the cap according to how they're supposed to be. That way, if someone else gets to work on your engine, they won't have to figure out what's wrong with the firing order. Or, if you end up with an even unrelated issue, you won't have to be concerned about how your distributor is installed.

One thing to consider is the vibration dampener is a two piece assembly. The outer ring is held to the center hub with a rubber intermediate ring. As a vehicle ages, the rubber can deteriorate and the outer ring can move, throwing the timing mark off. Not a common thing, but it's been known to happen. Worth checking if you continue to have problems.

If I were you, before I removed the old distributor, I'd confirm that #1 cylinder is at TDC compression stroke and confirm that the timing marks align. If you've removed the distributor after taking the above pic, one sure way to be certain is to remove the spark plugs (so that the engine is easy to turn over by hand) and the valve cover. Turn the engine over with a ratchet on the crankshaft pulley bolt until the #1 intake valve actuates and then continue turning the engine over until the timing marks align. That's about as foolproof as it gets.
Depending on which valve cover you have, the blue rubber Fel-Pro valve cover gasket is the most recommended VC gasket that I see here.
Then, install the HEI in the factory position.

What carb are you running. If you're running a Carter BBD (stock carb) you need to set the stepper motor needles per the Nutter bypass instructions and leave the stepper motor disconnected.

Let us know how it goes.

Good Luck, L.M.

 

Yeah that's the plan. I'm going to move it around to where it should be. Understanding it a bit more now after some research. I am sure that I am at TDC comp stroke. I have come to the conclusion that the last people to work on this engine (a high school class) just slapped it in there, then moved the wires to the positions where it would run. The carb is after market, no brand name to be found. No stepper. This is another project where I am learning a lot and enjoying the shop time. 40 more years and this thing will be ready to roll! Thanks for the reply.

 

Good luck, take lots of pics as you go for reference.

 

Got the HEI upgrade done. It went pretty smooth actually. It was a good learning experience, I have a much better understanding of how everything works. I got the dizzy turned back around where it should be, but once I started timing it, the wires were against the block and the vacuum advance was pointing toward the block, so I pulled it back up and rotated it a couple teeth. When I started this project I was pretty sure it would never run again. With this in mind I didn't clean up all of the wiring that could be removed just yet. I will trace them and take them out a piece at a time and make sure I'm not disabling something as I go. There are unused wiring plugs everywhere under the hood. The jeep runs fantastic. The plugs that were in it weren't gapped correctly, PCV valve was plugged and oil was leaking on top (didn't know what this was or how it worked,....till now), scrapped the factory air cleaner and cleaned up some vacuum lines. Electric choke wasn't even hooked up, will likely add a manual choke later. The bad news,......the new pan gasket I put on is leaking now. It just might have to leak this summer, we want to leave it at the cabin for the summer.