Replaced the PCV and grommet this evening with OEM parts.
Blew out the hoses, they didn't seem bad at all. Carb end of the PCV hose split, so it will be replaced soon, but is serviceable for now.
Noticed the air filter was about 50% saturated with oil when I pulled it. Didn't grab one, so I'll replace that soon.
Pressure gauge seems more stable, probably in my head. I'll keep an eye on it during my commute tomorrow.
I'm still very confused by the dipstick. When cold, I don't see anything. When hot, the whole thing is coated. When I pulled it while running, I was getting some exhaust out of the tube (seen it in the fill port as well). Next project maybe.