I still need to play with the mill a bit, ran out of time last night.

but if I can ask this,  is your explanation of "D8 TO A8 then A7 to D7 etc."  what your saying is the normal?

Maybe I am just expecting things incorrectly,    In my head, I see the drill bit moving like it was reading a book.  A1 -> B1, then B2 -> A2, then A3 -> B3.

But if I read what your saying, I have some core expectation that are wrong, which is good, because it makes sense why things are happening outside my expectation.

Well at least I am learning . 

Probably going to be going into work this weekend, so not sure how much play time I am going to get. 

I love this hobby!

Well if the way BobCAD V25 is doing the operation is the same as your V24 then it starts furthest right and nearest to you on the pocket, it then moves in Y away from you then along in X to left by a small amount (11mm maybe) then back on Y towards you then continues like that to the end.
Remember I am talking tool in relation to work rather than table movement..
Basically what I showed in the screenshots is exactly what you would see if you were looking from above the material.
Hood

BTW you can likely tell BobCAD where to start.
Hood