I always considered that the behavior of the device in my second presented thought experiment, would be somewhat like that of a projectile launched perpendicular, though I am now skeptical that this is the case.
If you consider the x axis (Parallel with track) and y axis, initially upon exiting onto the plane, its velocity may be described by these formulas.
(velocity in x axis) = (Track exit speed)  (  Deceleration due to drag)(Elapsed time after exiting track)
(velocity in y axis) = 4(  Deceleration due to drag)
(Magnitude of velocity)^2 = (velocity in y axis)^2 + (velocity in x axis)^2
= 17(  Deceleration due to drag)^2( Elapsed time after exiting track)^2 + (Track exit speed)^2  2(  Deceleration due to drag)(Elapsed time after exiting track)
From this formula one can determine that the net speed of the device increases over time and hence has gained energy.
This formula wont be appropriate for long based on the fact that the relative wind direction will change and lower the lift/drag ratio.
