Ken ,
I went back and I see what you mean. If you pick the outer boundary first then the islands it plunges one way. Then if you pick the islands first then the outer boundary it plunges an other way.
I've never picked the islands first so I've never run into this before.
Why don't you put some points on the boundarys to guide yourself (ie: always start at top outer boundary then work your way down inside to island say right to left, top to bottom.)
And your right about the marked drill points, it puts then in for you to generate your drill pattern. I Should have read the message box.