A 4 stroke v twin engine should have very little crank case pressure or vacuum. As one piston goes down, the other is going up, so there is about the same air volume at all times. If an engine had NO LEAKS, and the crank case breather was properly routed to the air filter there would be negative pressure at the dipstick. As an engine wears you start getting pressure leaking by the rings, and valve seals (in the case of a flathead engine like yours) which cause a bit of positive pressure. This is where a leakdown test is helpful. The breather assembly has baffles to keep oil out, and is located high in the block well above the oil line. all that should push out is the airborne oil vapor. Typically with the breather into the air filter, this vapor is burned off with the air/ fuel mixture. If you are getting fuel contamination, your oil gets thinner, and therefore vaporizes much easier.
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