Hard starts after running

If I was in your situation with a low cylinder pressure 318, I would run at least a 2800, and 3.23s.
You'd get a similar hit off the line, a quieter ride, better fuel-economy, and possible even the same or similar zero to fifty ET, cuz the 3.23s will get you there without a gearchange.
3.23s will get you about 65=2700 with 26" tires at Zero-slip/perhaps 2800 with a 2800 Tc and 3>4% slip.

Oh wait, I already did this, lol. and loved it.
I'm not getting too carried away until I decide the future of this '69 340 in the garage. In the meantime, I'm learning as much as possible. My winter plans are, chassis stiffening, rear end spring perches, might change center section, maybe torque converter or transmission. Whichever is janked up. Both...

but right now it's timing and carb since I drive it as much as possible.