Well turns out the issue with the timing I was having was because the distributor was having issues. When I upgraded to HEI it was the 'DIY' version where I picked a distributor from an appropriate vehicle and installed it.
But what happened was as I was driving to work it just totally died. So I called my brother and he towed me back home because I was only like 2 miles away when it died. I pulled the distributor and the gear fell right off and down into the oil pan :/
After pulling the oil pan, which is a story in itself, I found small brass pieces and of course the distributor gear. I then remembered that the gear didn't fit exactly right so I took a brass bushing and cut it down as a spacer. Well it appears that it's not durable enough to work well, and after the spacer broke up (which is what caused the timing to jump) the movement of the rotor up and down caused the pin to shear off.
I ordered a new 'official' HEI distributor from 4WD and put it in yesterday, and it's running like a champ now!!