I'm not sure I follow that...rolling start for the Ford is just a way of getting the whole ICE disadvantage out of the picture - and it would make the demonstration of the electric motor advantage more impressive! Plus the CT would get a little bit of free energy transfer via regen, from the Ford, initially.
I kind of feel like it should be fine for the Cybertruck - it simply then progressively increases the load on the F-150, and if it's strong enough, it should be able to stop it (or make it break traction whereupon the F-150 would lose).
I don't see how momentum has much to do with it...in the end if the Ford is pulling the system at a fixed 1-5mph or whatever, it's just a question of whether the Cybertruck can accelerate the system in its direction. That should be possible if it can outpull the Ford. But maybe I'm missing something here. I guess I'm starting to get a bit confused...