Mr Phelps, you haven't returned any responses lately but the random nature sounds like trash in tank could be the issue or shorted wiring but the wiring doesn't jive with your dirty filters.
At 250k you don't say if it's the orig lift pump but if it is, that thing has lived it's life too.
Best way to diagnose the pump and or blockage is with a fuel pressure guage upstream of the injection pump. IMO don't waste your $ dropping the tank again until you can replicate the problem and see a loss of fuel pressure.
If that's not the culprit and you have positive pressure after the fuel filter when it dies then could be a bad fca dropping pressure on the high side causing the Ecm to not fire the injectors.
To me this send more likely if it stalls like you turned off the key.
Are there any stored codes?
