How hard would you have to push down on the board to hold it in place?
You don’t push down, you push forward – well, hold it from moving backwards, which is the same thing – with a force equivalent to the wheel drag.
If you pushed the skate board on a static conveyor would it behave in the same way?
If you pushed the same skateboard, with the same force, on a conveyor that was now static, it’d move forwards at the speed the conveyor had been moving.
if you pushed the skateboard gently only, which end would you expect it to fall off?
How gently? If the force you push at is greater than the wheel drag, it’ll fall off the front of the conveyor. If it’s less, it’ll fall off the back.