“…and what does go in comes out completely oil free.”
That is expected. If you can’t get it in all the way except for about 2 inches, the dipstick will not get wet. I wouldn’t worry about that at all for now. It will only become a problem when you really do need to check your oil level. Try pushing something like a thin wire through the tube and see if it hangs up in the same place. It has to be thin enough to pass through a hole in the blockage that the dipstick can’t, but it still mist be stiff.