Couple of these; You had your lead-in settings set too high and it was recognizing the collision that was going to occur. You also had your angle set to 30 degrees, for some reason. Personally, when working with circles, I prefer to set my Lead-In/Out angle to 135 degrees, somewhat mimicking a "return to center" type move that you would find in the Circular or Bore milling operations. I also reduced your lead in to prevent collisions.
Now, onto the issue of the Back Chamfer. This is one operation where math gets you close, and then fudging and guessing gets you the rest of the way. Once you get it set perfectly, do yourself a favor and save that as a template so you don't have to go through the whole mess again.
Chamfer mill (regardless of how there are defined) don't yet recognize cutting on the upper side. You have two options if you want to cut a backside chamfer:
1) Math and fudging "Stock to leave" and Bottom height Offsets
2) Dovetail Mill and select the bottom contour of the chamfer. Also using Stock to leave in the Axial and Radial
Take a look at what I did for your part and let me know if you have any questions
Seth Madore
Owner, Liberty Machine, Inc.
Good. Fast. Cheap. Pick two.