Small update. I have decided to switch from usb type c to usb 3.0 micro b.
I think I figured out your USB type C problems. After messing around with my own breakout boards and cable, I found the cable itself connects multiple pins to each other (using four pins for ground, and four for Vcc), and "rolls" the connection from one pin to another depending on the cable's orientation.
A2 on one end doesn't go to A2 on the other. It goes to A11. Or if you roll the cable, B11. From it picture (if color is meant to match) it looks like you've got a lot of X:X connections.
There are two pins which (depending on orientation) are 1:1 matches, but the rest go elsewhere and need to be tested for.
After mapping things out, I found in one orientation I could get 11 connections, which meets my requirements, but leaves the cable non-reversible. Also, flipping it the other way seems to only give me 10 connections, as CC1 doesn't seem to connect to itself somehow...?
Hope this helps anyone else considering multi-pinned connectors for hardware connections.