Great points...
This will be difficult for me to persuade you into towards my opinion on this..mostly because I suck at explanations, and there is no true way to prove my points...but I will try...
first of all...it totally depends on how different the gearing is betwen the runs...In all honesty, I feel that a the first two combinations you mentioned in the same car will run a 1/4 extremely close to each other...there is not nearly enough of a difference between the high hp car and high torque car...
But the gearing thing...torque is multiplied by gearing, so with shorter gears, you have more torque to the wheels...hp is not, since its a rate based on time...But lets make this easier...say you have two engines...on makes 200lb/ft of torque at 3500rpm, and makes 100bhp at 7000rpm, which is the redline (not a very likely combo, I know)...and another engine making 100lb/ft at 3500rpm and 200bhp @ 7000rpm...and both have a close ratio 6 speed gear box...
Now in order for large amounts of torque (force of rotation) to do any work, you need to have very long gearing...the long gearing allows the car to accelerate down the road...with very close gearing, like say short enough to only get 20mph out of first gear (not uncommon for some extremely close racing boxes)...you get...wheel spin...and thats it...the torque to the wheels is so great that nothing happens in the form of acceleration until the next gear...then you accelerate through second ok, and third ok...but remember the powerband, at the time that you are shifting after first gear, the car is not dropping back into its torque band...you are slow...
At the same time, this is an ideal box for a high hp/low torque engine...the close ratio allows first to be eaten up fast, despite small amounts of lowend torque...then the engine is making lots hp, and to do work with torque at a high rate, you need short gearing...so the car continues to accelerate hard through every gear...
Now the other way around would be with an extremely long gear box...one in which you could pull 40mph out of first...the low torque car would use this lower gearing affectively to do considerable acceleration with a much slower climb in rpm...that is what torque needs...torque is instantaneous, the longer the engine holds that rpm, the more work it does...with long gearing, the engine stays on 3500rpm longer...so it accelerates longer...and being that the gearing is spread out, every shift change brings the car back down into that torque zone, and continues to accelerate hard...
on the other hand, the high hp car could do nothing with this gearbox...and barely get rolling, because it was relying on high torque multiplication through the short gearbox to make up for its small torque output...not only that, but after first gear, the revs would drop well out of the power band...it is misleading to put a certain hp at a certain rpm...because to do work, at least in automotive instances, needs to sweep through a band of high power...so when you have short gearing, the car can continuously plow through its powerband...and still accelerate...but without the gearing, and without the properly matched rev falls after each shift, it has trouble...
These are two extremes...which is why I said theoretical...but because of this variable, I can't say that a high hp car will always beat a high torque car...