Paul...
All of what you wish for should be easily attainable. Developing an index system for 2 sided machining is commonplace, should the part require that. Think of 2 "stations" if you will. One where one side is completely machined and the parts outer profile is cut. The other where the removed part is set into a machined recess for the flip side machining.
If you proceed with CNC routing, you will find that part or material hold down is a significant portion of the process. There is no one method that works for all operations and all hold down methods have drawbacks. Its all part of the learning curve. Rest assured that your part is more than doable. That said, I am not sure that I would set up a second machining station for a simple chamfer that may be most efficiently done with a table mounted router unless there were additional operations on the flip side of the part.
Gary Campbell
CNC Replacement & Upgrade Controllers
Custom 9012 Centroid ATC