...Starting to believe it’s not an air leak as it runs fine once you get it going...
IMO, you just answered your own question. I've had my share of chasing an air leak for a while. However, the key symptom was generator shutdown after running for sometime (30min, 1hr, 2hrs...no consistency).
Based on my experience, I can't imagine how the genny can run fine if you actually had an air leak.
Your interpretation of the genny "running fine" could be not exactly valid. It may sound fine, but you can't be 100% sure what's going on inside until you do some detailed investigation.
To solve your issue, I'd start following the logical chain:
1. Does the lift pump deliver fuel to the specs? - sounds like yes, since it gives you enough fuel to keep the engine running, once it starts.
2. Does the high pressure pump deliver fuel to the specs? - you'll have to take it to the qualified shop for 100% answer. However, you can do basic visual test by opening each port and crank the engine to see if there's fuel coming out of each port. If there's anything abnormal, you should be able to see it.
3. Does the fuel get properly delivered to each cylinder?
4. Does each injector operates to the specs? - you'll have to take the injectors out and bring it to the qualified shop for 100% answer. BTW, the same shop should be able to service your HP pump and injectors.
5. Does the fuel freely returns back to the tank?
Until you start checking the items off the list, one at the time, we obviously won't be able to solve your problem. But depending on the age and the hours, I'd be focusing on items #2 and #4. If the HP pump doesn't deliver fuel 100%, you would not hear it. If an injector is not operating 100%, you would not hear it. That's where professional shop comes into play.
Lastly, let's assume that air got into the system. If you locate a bleeding valve on the HP pump, you can loosen it and let the air escape, until you see clean and bobble free fuel flow. If you don't see any bobbles, then theoretically, there's no air in the system. In any event, once there's clean (air free) fuel is getting to the HP pump, there should be no reason for your genny not to fire up quickly. If it doesn't, it's clear that the problem is elsewhere, meaning that you should be looking at what I've described in bullet-points above.