Based on another (mis)interpretation of what we see, what happens if you Ctrl/Cmd+E (hold Ctrl or Cmd and press E), toggling between GPU and CPU (you can untoggle if the issue remains)?
Are you completing the path before its outlined? it sound like you are trying to flatten the path. if your working in live paint first you will need to expand the live paint.
Illustrator is open almost 24/7 and just about the same for Bridge and Photoshop
And please show the images by using the Insert Photos button (looks like moon over mountains) at the top of the reply box which makes it appear right there in your post together with your text, rather than the more conspicuous Drag&drop attachment which requires helpers to open a new tab and wait for its showing, then go back and forth; and if they just click it and wait for its showing and press the X to get back to the text the image is gone so they have to open it again and wait to see it again.
Just to be on the safe side: You know that offset Path creates a new additional path with a (positive or negative) offset/distance to the selected path?
AdChoices