In SheetCAM select the "Edit Start Points Button" then right click the part and select "Quick Cut Sequence". A small window opens up showing a number. Now just click on the start points in the order you want them to cut.
If all entities are on one layer, SC will automatically figure the inside contours and do them first. I've never seen it mess up there. Like TP though, I also tend to put different contour methods on different layers. That just gives you more control.
The other thing that can cause the automatic thing to fail is if the outer contour on the part...and there should only be one...is not a closed contour. If it's not closed, SC will not see it as an outside contour and will not set the order to cut it last.