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Those O-rings are shot. I don't think that will impact boost and gets (that is usually a leaky up-pipe or loose boots) Those O-rings will impact the way the motor runs/sounds/vibrations.
I think the idea was that the bad o-ring was preventing it from making peak power.
I've had a black outer fuel filter for a while. However, that lower o-ring wouldn't cause oil/fuel to mix int the fuel rail would it?
Also, what about cleaning out the cups - there may be some o-ring residue on them. A rag with solvent on it?
That's not alot of miles, if it was 200K I would say "hell yeah, I would". But at 140K, that's a gray area. you could do it when you put new injectors in her down the road.
Did you check the torque on any of the injectors prior to removal? If so, were any of the injector hold down bolts extremely loose?
Yes I did. Before doing the compression test. #3 or #5 was a little loose. More than 55 inch lbs., probably in the 80-100 range. The bad O-ring was #5.
Crap.... I'm late to this party. The answer to the cup question is: "With the injectors out, conduct a coolant pressure test." I actually remove the coolant and inject air into the system, this allows me to look for air to leak out the cups, not wait for an obscure coolant drip. Pass the test? Move on.
Oil will absolutely get in the fuel rail with bad O-rings. The oil is about 1000 PSI at 60-65 MPH on the flat with no wind, and the fuel is about 60 PSI. Compromised O-ring = black fuel filter. I don't see signs of a loose injector - the stains are just from fuel slipping past the O-ring and camping there with heat. The copper washer did it's job. If it didn't, you could expect to see soot where those stains are.