Some tips to start out with,
1. Attach your new file with the additional operations you had mentioned.
2. I would always set up the stock to be at least .015 above the model top so that you are machining into fresh material and taking care of any irregularities in the stock (you are working with dead tree carcasses).
3. Machine the inside pockets, Drill your holes, then adaptive or pocket the exterior around the body with stock to leave.
4. Then do your parallel / finish contour passes with the last one being a 2d contour with tabs. then you can just saw of the remaining stock.
5. You have the 4 holes that you can locate off of for the back side but you'll have a hard time holding that without machining a negative to place the front on. You should really plan that out before you go cutting with your good stock.
6. About that, I would get the operations so they seem to work like you think they should. Save a copy of the file then scale it down to something 2x4ish so that you are using some cheap stock and not wasting plywood experimenting.
7. You said you set your tool right, but did you check it after the cutting started? did it maybe get pushed in? If looks like you have some burn marks in the lower part of you picture so maybe the bit was not cutting well and got pushed in? I would check the feeds you have. At least with file you provided the feeds were way low.
8. For a parallel path you probably want a ball mill.
I attached a general idea of what I would be trying for, the mill can get to all locations because it is not long enough, needs drill bits, slow feeds etc.