Your miss sounds like you might still be running lean. What carburetors have you tried? If it's a Holley you might want to try taking the jets up 2 sizes at a time until the popping goes away.
I'm not sure what you mean by needing bigger combustion chambers than the Twisted Wedge heads provide. I run flat tops with standard 4 valve reliefs and a set of Twisted Wedges with no problem. The problems come with piston to valve clearance if you run a large cam. My cam with the 1.7 rockers are just below the threshold of Trick Flow's recommended max lift, your cam is smaller assuming you're sticking with 1.6 rockers, so they wouldn't have been a problem. The Edelbrock heads will serve you well and be a substantial improvement over the D8 heads, I think you'll be happy with them overall. I don't have any first hand experience with that cam, but I'd venture a guess that with the rest of what you've listed you'll be happy with it as well.
As for the damper a replacement should be just fine as long as it's the correct 28oz balance and not the later 50oz. And it'd probably be a lot safer than the old damper you have that sounds like is dry rotted.
Your rear end housing sounds like it needs replaced, so if you have another it wouldn't be a bad idea to do so. It probably could be welded to seal the leak, but a replacement would probably be a better option.