Solidworks is probably the easiest software to learn. If you have any background in AutoCad the transition is easy, if you have experience in just about andy 3D modeling software the transition is even easier.
You can always get DWGEditor from Solidworks (there copycat autocad program) and...
You should be able to mate the edge around the cup on the set screw to the plane of the motor shaft using the distance mate......but you wanted to do it a diffrent way???
I dont see how you would be able to do this without creating some additional planes that probably wouldnt be needed for...
