To update my post, I've now got the old girl ticking along smoothly. It turns out I had more vaccuum leaks than the liberal budget. The new dual carter/webber carb I got was also at issue, we just couldn't get it to idle, so we switched back to the original rochester. A tweak of the timing and distributor and she's good to go.
Now comes the hard part, up here in Vancouver it needs to pass a vehicle safety inspection. That said, 1958GMCnut (if you are out there) what has your experience been? Can you recommend an inspection site that has experience with old bolts? It's just another cash grab before I get it in for air care.