For the "pain in the neck ones" you can also select the closed entities, move the cutting start point to somewhere else on its profile ( click again where you want it to stay).
When you post code make sure you turn off profiles / chains not wanted.
What is causing the pain is that LC is automaticaly selecting the start point, but, when trying to create an offset at those points it senses that you will not stay on profile ...i guess ? and thus either dosen't do the pathing / rounds / or changes the path " to help the user avoid a machining error".
RICH