Can this be done in Carbide Create?
It’s not automatic, you either have to add a second tool which lies about the endmill diameter, or draw in additional geometry and cut thusly. Discussion of the latter at: Adding geometry to cut as a pocket with a finishing pass
Can the same line have two different tool paths? Or would I add another line to accomplish this?
Yes, you can assign multiple toolpaths to a given line or combination of lines.
Thanks for all the help. This is all so new to me.