I was thinking a hub motor could be mounted to a large, industrial type caster which would be equipped with stops to prevent the wheel from flipping all the way around and shearing the power cable. However, you bring up a good point with how the caster might react to the motor torque. I had not thought about that and maybe it wouldn’t work at all? I noticed the electric rip stick doesn’t use a caster in back. I tried ordering one on Sunday but due to the battery, no one will ship to Alaska.
I don’t know if I’m that enamored with the float feel on the OW. It isn’t really like snowboarding, except in powder and even then that feels different. All in all I generally find the teeter totter feel a bit annoying, except when slowing down quickly, that feels pretty natural. Leaning forward to go up any incline is pretty screwed though.