If you can start it when it's warmed up does it act like it's flooded with fuel when it starts?, black smoke? Have you checked the static ignition timing to make sure it's not too far advanced? I wouldn't worry about the clear fuel filter only part full when running - that is very typical. Yes, some residual pressure in the fuel line is normal. You are correct with the assumption of fuel in the oil and the engine "making oil if it were leaking much into the cylinders. Also what Jerry is saying about crankcase pressure finding it's way into the carb/fuel line is right - can't happen.
1957 Chevrolet 5700 LCF 283 SM420 2 speed rear, 1955 IH 300U T/A, 1978 Corvette 350 auto, 1978 Yamaha DT175, 1999 Harley Davidson Softail Fat Boy
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