Well, replacing the olives fixed it.
Well kind of.
Nobody had olives. No parts stores had the pump install kit, no ag shops in the area had anything, I didn't have time to order from one of the vendors or mcmaster carr, and it had to run Saturday night. So the hardline from the pump to the filter head was replaced with brass fittings and barricade fuel hose we keep in stock. I also used crimp type fuel injection clamps, which are better then worm drive hose clamps, so I'm not worried about it leaking fuel or air.
Plus, putting these fittings on allowed me to check fuel pressure. Which I wanted to do since I installed a check valve in the supply line, and some on here stated that they might restrict flow too much.
No issues were found. Fuel pressure was maintained at 5-5.5 psi the whole time, and being in a bus, full load/throttle is pretty much the norm. So I'm confident the check valves aren't causing an issue. Oh, and the fuel psi maintained 5 psi for several hours after shutting the engine off fwiw.
The good news is that I started it today after sitting since saturday night, and it fired right up, where it would typically start and die, so I'd say the problem is fixed.