Maybe I missed it..but how much did you pay for the car?
because he literally placed a 305 block in the trunk for the entire trip.
I don't have much experience reading plugs but I would say those look like a heat range too "cold" for the level or frequency of boost you're running. I think that black crud should be burning off if the plug is heating up enough. May not be an issue once you start driving the car hard though.
Unless that bottom barb is the drain, don't you want both fittings to be near the top of the can, air in, air out, let the oil fall? Otherwise the oil will eventually reach the level of that bottom barb and start pouring down it.