@ClockworkOcean @Chatouille thank you both for your answers! You are both correct to point out that I should use box collision here, it totally slipped my mind. Thanks!
I did however end up dwelling on this topic a bit and using both of your answers I went ahead and played around with some different composition and traces. The result: @Chatouille is right with his second point: The order of the hit results and the impact locations, normals, etc. depends on how you trace. This playing around and trying out some of your ideas really helped! I will make a discussion post with all of my findings and link it here for those looking for any more detailed info.
On a sidenote, @Chatouille your first point i did not really understand. My current understanding is that shape wise you can achieve the same by just using one big shape, rotated how you want or repeating a small shape over and over again in a linear way from start to finish, no? This is not a crucial point, but if you feel like it would love to hear more about what you meant 
I’m off writing the discussion post, thanks again!