~~D'oh - yes, that formula is true only if the triangle is right-angled, which is true for only a single base length.~~
Edit: Actually, this is always true: we are considering a right-angled triangle where the base is the horizontal distance from the ground station to point under the satellite, the vertical part is the 550 miles between the point under the satellite and the satellite, and the hypotenuse is the line joining the satellite and ground station.
> if a sat is 500 miles up directly overhead that's the closest it ever will be, as it flies off the hypotenuse gets longer
Yes: as the horizontal distance d increases, then the length of the hypotenuse (sqrt(d^2 + 550^2)) increases.
However, the difference between this and the horizontal distance (sqrt(d^2 + 550^2) - d) decreases.
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If the angle from the horizontal to the line between the satellite and base-station is theta, then:
sin(theta) = 550/hypotenuse => hypotenuse = 550/sin(theta)
tan(theta) = 550/base-length => base-length = 550/tan(theta)
difference in length = 550/sin(theta) - 550/tan(theta)
[which simplifies to 550 tan(theta/2)]
We are interested in angles between 0 degrees (horizontal - corresponding to the limiting case of infinite horizontal distance between the satellite and base station) and 90 degrees or pi/2 radians (straight up): https://www.wolframalpha.com/input/?i=plot+550%2Fsin%28x%29+...
This is always between 0 and 550.
The triangle inequality holds: for a single hop from base-station to satellite, the increase in length is never more than 550.
But as you point out, there may also be multiple hops.
> So ideally you bounce off a sat overhead, (distance of 1100),
This is the shortest total ground-satellite-ground distance, but as you cover 0 horizontal distance it is the worst case: the difference between the ground-satellite-ground distance and the length of the direct ground-ground line is maximised.