Ideal machines, such as a frictionless plane, do not change the work done because the force the work is being done against is conservative. We use machines because it changes the distance that we apply the force through, so the product of force and distance is still the same, thus the work is the same.
The picture of non-ideal machines is somewhat different because the forces involved are no longer conservative. Therefore, the work done is more than it would be if you were using an ideal machine.
For the block on the plane question, think of it this way. For an ideal machine, the work done is just change in the energy of the system. You take a box from rest and lift it to a height h and you do mgh of work on the box. That amount of energy is constant, regardless of how you get the box there - you can move it up a ramp, use a pulley or a system of pulleys, whatever you want to do. The total amount of work you do will never change because gravitation is a conservative force. If you add in friction that changes.