I think the pop off pressures is fairly inconsequential here. I've run injectors at both VP and p-pump pressures (not the conversion injectors like F1's, mind you), and my last set of VP injectors actually run the best. That being said, your injectors may be in rough shape and wouldn't hurt to be refreshened.
Fuel pressure shouldn't be hurting you. I ran mine with the VP setup for months with no ill effects. 18-20psi both at idle and WOT. I am wondering if your airdog is just a pump, or is it a filter/water seperator/de-aerates the fuel? If its just a pump, you could be sucking air in the tank giving you fits at the pump.
How did you find TDC? Never hurts to double check.
FWIW, a friend put a '95 12v into his chevy truck. Engine ran fine before the swap. When he installed the engine, he retimed it to 16 degrees (6.4mm). He checked before he changed it, and it was at something rediculous like 28 degrees. Truck never ran right after that. Even changed the pump to a rebuilt one I had. It would start fine, but around 1500 rpm it would start blowing white smoke and you couldn't get it past 2k rpm. Would pop and break up and the smoke would burn your eyes. Got a set of good injectors put in there (DDP4's), and it was a night and day difference.