Apologies for not following up here to your statements. While it is true that using a tilt stage is enormously useful for this kind of work, it is not nearly prohibitively difficult to NOT use one. Until it was invented and now for anyone not flying one, we train our post hand to compensate for the horizon roll inherent in side to side work, especially rapid shots typically offered during a live concert when you are in the "pit" in front and below the talent/band.
It's very useful ( as always ) to practice this work. You don't need a stage or a band to do it. Shooting 90º off of the axis you are walking is a great thing to practice. Some folks are very comfortable side-walking. I'm a big fan of walking forward and aiming the camera 90º off to the side. Do what works for you, but when you find a relationship to the post and sled that seems most comfortable, practice moves with it.
The details of rigging the fiber cabling and having good wranglers are best left for another thread ! How did it all go?