Planning/selecting toolpaths

Hey all, I am new to MC and I am having trouble selecting the correct toolpaths, and planning out different cuts. No faces or edge combos give me what I want. If someone could lead me in the right direction that would be awesome. Thanks.

Here is the part I am trying to cut:

Attachment 233878
Attachment 233880

My planned first cut is to use a .5 end mill to take some material out of the middle of the C. How would you chain/select/make this tool path?

Attachment 233882

Once the middle material is remove I plan to cut the outside profile.

Attachment 233884

Then the final cut for this op would be the chamfer, which I have no idea how to do.