Ah. I was really trying to avoid a DIY cable, which is why I wanted two connectors through each side of the wall. I have 0 knowledge when it comes to wiring, nor the tools to do that.

My original plan was to buy a pre-made 50ft cable, another 10ft cable, and have them connected through each side of the wall.

The 50ft cable will be somewhat bent, probably 60-70 degrees, when I go around my door frame. I plan on putting the cable in a wall cable cover.

Still won't work?