So I think my Ignition Coil Ballast died! I've always had trouble getting it started but it started getting progressively worst over the last year until I wasn't able to get it started at all. Took forever to figure out what was going on. The Ballast apparently limits the current going through the coil during normal operation to save the points. When starting however it should bypass so you get full current and a stronger spark. The latter wasn't happening anymore however so it was getting incredibly difficult to start. I've got an on/off switch in there at the moment to bypass the ballast when I'm starting the car. More updates when I find a replacement!
I had a DUI HEI distributor in my last truck, best thing I ever did! Super easy to hook up, super easy to get parts for (never had to, but it's the the same as gm hei) and definitely a good performance setup. Definitely got what I paid for, will do it again if/when I build my project car.
Theres a write up on here somewhere to swap over from a points dizzy to electronic(or whatever it is)