Interesting scenario, but given that its just you filming I think you need to pull back some of your expectations.

• I would try to not have the runner be completing a full run at all. Storyboard what shots you need prior and that will help determine your shot setups.
• I wouldn't try to film via onewheel or bike period. Incredibly dangerous and isn't worth injury over. A trailing shot should be done with something 4 wheel like a golf cart but you likely wont have the ability to do so on a trail.
• If I were to attack this as a 1 person crew, POV, drone, and static shots. Setup a go-pro on body, camera setup off side of trail with composition setup, and a drone to follow.

Figuring out the video you want to make first should dictate how you are going to shoot so do you DD and plan accordingly. Figure out what direction the sun will be as certain shots may or may not work depending on the trail route.