Congrats on getting the headers on that monster!
Initial timing doesn't mean anything WRT power production. What does your ignition curve look like? I'd try to build a curve that got 34 degrees of total timing (initial plus mechanical, no vacuum) at 2400-2600 RPM. Try to get a distributor kit and set up the distributor accordingly.
Did you make any carburetion changes? Often, headers increase the efficiency of breathing and require the carburetor to be jetted a little richer.
The need for backpressure to make power is an old wives' tale. If the headers are designed properly for your camming and the other tuning aspects are correct, you should make more torque and power with the header than with manifolds. If that old wives' tale were true, don't you suppose that racers would be running restrictive exhaust systems? FWIW, on one of my cars the supposed experts in this state told me that the header I was going to run was way too big and that I'd lose power. After I got the exhaust setup and tuning done, I gained .15 sec. in 60 foot times and 4 MPH on the far end of the quarter mile over the suggestion proffered by those "experts."