If you're using a large tool, the precise cursor will stay as a cross-hair, but the outline cursor will grow to reflect the approximate size of your stroke. If your tool size is very small, the outline cursor changes into the precise cursor so it isn't in the way.
Which tool are you using with the precise cursor that doesn't appear to be starting on the cursor?
What we try to do with most of the tools is start the stroke as though the centre of the tool is on the precise cursor. So if you have a large round crayon and start a stroke, the circle that is the size of your crayon would be centred on the cross-hair. So the stroke will actually start one half the diameter of the tool back from the cross-hair centre.
ArtRage isn't intended to be a precise application - there is a fair amount of chaos in the system to give a more real-world look and feel to the produced work, rather than a plain digital look.
AndyRage's mantra for graphics engine code:
"Sure - how hard can it be?"