Head gaskets go in a variety of ways, since coolant passages are closest to the cylinder disappearing or boiling coolant is a nice first symptom, but as the gasket withers is will spread to the oil passages next. Your plugs are the best indicator, there'll be a wet or white one near the area. Sometimes a leaking intake manifold will let some in there and there'll be multiple white or extra clean plugs. But water in your cyliinders will lead to scoring and excessive ring wear so you shouldn't let it go. THe pressure pump is good because you can pump it up, take all the plugs out, turn the engine over and coolant may spray out. In my Dodge Ram though, I thought a blown gasket was the problem, it turned out to be a pin hole in the hose that went over the rear of the engine, each time the engine was hot, some would piss out on the rear of the engine and evaporate. The discoloration on the oil cap is most likely from blow by of antifreeze in the cylinders (coolant getting by the rings). When the gasket goes to the extent that coolant is getting pushed into the oil passages, the oil with be milky. You want to catch it before it gets this far. At any case, after you do the gaskets, be sure to put some Marvel mystery oil in your oil, run the engine and drain it all out and put in new oil. You want to be sure you rinse as much water and sludge out as you can.
Bill