There are two answers to that question:
1: trust me it does. or try it yourself. with the top link jack screw all the way in or your hydraulic link all the way in. put it in the bottom hole and hook on a rotary cutter or some other long implement where it will be the most noticeable and measure the tailwheel height then put it in the top hole and measure it. The bottom hole will raise the tailwheel higher.
2: It is geometry. The geometry is a parallelogram. the toplink is the top of the parallelogram, the lower links the bottom, the left side of the parallelogram is the fixed height of the measurement of the pins and the top link hole on the implement. the dynamic measurement of the right side of the parallelogram is the height measurement of the pins where the tractor end of the lower link arms fasten on to the tractor and the holes where the top link will fasten to the tractor. Your choice of top, middle or lower hole. If you choose the lower hole the right side of the parallelogram will be shorter and as you raise the lower link arms they rotate around the their fixed pins on the tractor, and since the top link jack screw is turned all the way in, the left side of the parallelogram will tilt more toward the tractor which will raise the tail wheel higher off of the ground. If you don't understand all of this, see answer 1 above
James K0UA