Here's an example of what I don't want, vs what I want. (ignore the fact that one outline is lighter than the other, it's the overlap I'm concerned with)

And the only way I can figure out how to implement it is by creating two objects and putting them right on top of each other. (along with whatever design I'm using)

Trouble is, this is a real pain to implement, especially if it has to go over/under other objects. And Editing it afterward is also a real problem. So I try to make really sure that's how I want it before I create the second object.
Is there a better way to do this?
((I apologize if this is a redundant question. I've found things that seem similar, but not quite the same as what I'm asking))