converting points to hei on a chevy 283

Pretty sure the Chevs used a resistance WIRE to feed ignition. This means the original ignition feed is going to be low voltage.

Where are you getting 12V from?

Is this a stock GM HEI that is coil in cap?

I do not remember, anymore, if you need the starter "I" connection or not. What you need to do is monitor the ignition "run" voltage and see if it remains hot in start. If so, you don't need the extra wire from the solenoid.

HOW to time it. Pull no 1 plug. Put your finger in the hole. "Bump" the starter until it STARTS to blow your finger out. You never done this? Might take a trip around or two to get the feel. As soon as you feel compression, pay attention to the marks. Bring the marks up to 10-15 BTC. DO NOT set at TDC. Drop the dist. in with rotor pointing to the no1 tower, and the vacuum can "about where" you want it.

IF THE oil pump drive won't seat, don't worry. Just bump the starter until it seats. Then, bump it around "to the marks" again and check timing, which will have changed some as the distributor dropped. If it's "too far" to adust with the vacuum can in the way, simply pull it up and "walk" it a gear tooth one way or other and check it again.

This is easier than it sounds.

YOU CAN SET THE TIMING "on the starter."

There is no reason to go through the "180 out" nonsense. You should be able to drop it in and start it up.

If you are fighting timing issues, or there might be something wrong with the ignition (distributor) then "ignore" the wiring. Just "hot wire" the distributor, get it running and timed, and THEN deal with the harness issues.