Version 1 was a good experiment and I'm happy now that this product exists but this design suffered some problems and needs improvements for manufacturability.
My thought process was that I could sand down the pins of the 2x5p header enough so that it's solder points wouldn't interfere with the dual USB ports placed on top of it. This works, but creates a problem where some pins don't get enough heat because they are below the surface. This means we're heating up the pad and flowing solder around the pin. Since the pin may not be directly in contact with the soldering iron due to being slightly below the surface of the board, it may not get hot enough to accept solder. Soldering at a fast pace results in quite a few failures and with rework, I've only managed a 30-40% success rate with the first batch of 100 components.