Any 2 stroke experts out there

That's right;
some of the oil, maybe most, goes out the pipe with the hot exhaust. But some condenses in the system and eventually plugs the spark arrestor, if equipped, and or the baffle.
In the past we removed the tuned pipe poured diesel into them, stood them up, and set them on fire. Later, we retrieved them, cleaned the outside, hit 'em with Hi-temp paint, and re-installed them;
instant tune-up.