I feel like there are three main factors to this question you are trying to highlight...
- The strength of each person
- The height variation of each person
- The amount each person leans when pulling the rope
Let's look at this as an ideal situation to your proposal. The strength of each individual are the same, the height variation is a steady slope, and the leaning of each person continues this steady slope. The other thing I will do to diminish variables is make these individuals pull a rope attached to a wall.
The X direction is the force of the team pulling in one direction and the force of the wall pulling on the team in the opposite direction. (I am generalizing the equations, there is also tension, but the total force in the X direction is zero because the wall is pulling back with the same force) THIS WILL BE THE SAME NO MATTER WHAT ORDER THE TEAM STANDS IN
The Y direction, however, is where your question gets interesting because one thing I did not account for in the X direction is the force of friction of the shoes on the grounds surface.
Now the force of friction is equal to the normal force times the coefficient of friction. The normal force is equal to the weight of each person, in this particular case (mass times gravitational acceleration).
This means that the height of each person does not affect the force to pull the rope, it actually has to do with the total weight of each person and there individual strength.
Edit: Each person is trying to pull the rope horizontally. So lets say we use your example where the short person is in front. The tall person in the back is trying to pull the rope horizontally, it would be wasted force to try and pull it at any angle other than parallel with the surface.
The fact that the last person is taller will put a slight force in the upwards direction of the shorter person (very insignificant) Now if the tall person was in the front he would have a slight force pulling down (the same force as the short person felt only in the opposite direction)
These two forces are very insignificant compared to the weight of the individuals that their heights would have to be that of a toddler to an full grown adult, and even then the force would still be very small.
So yes the heights would make a difference in an ideal situation but even then it would be very very minimal.