Great thanks Chris!

After looking at similar post I think my solution will be to directly solder the wires onto the J1 limit switch so I don't have any clearance / bending issues.

I found the problem and I am documenting it here: https://www.anninrobotics.com/forum/questions/shorted-5v-connection-because-of-bent-j1-limit-switch-terminals

Never mind ^ I have a shorted wire somewhere on the robot wire side. All USB ports offer overload (implies short-circuit too) protection so that is why my Teensy would disconnect. Using a multimeter I found that I have continuity on the red and black 5v wires. Visually all the red wires go to red 5V and black wires go to black 5V so this will be fun to debug. Sorta wish I took the time to redesign / make the robot wiring a little more fool proof and easier to work with (wiring is really tight and hard to visually and physically work with). I'm open to suggestions but I think my only path forward is to start undoing all the robot arm 5v wiring until I find non-continuity because visually all the wires match up with their correct color.

The Teensy 3.5 is expecting an input when I connect a wire to the Vin pin and disables power from the usb. The current wiring schematic in the manual and explained above does not work with this Teensy logic. I'm slightly confused on why this has not happened to anyone else on this forum. Did I miss a step that disables the Teensy 3.5 Vin pin logic?