I figured it might drive inverted but its hard to tell from the CAD angle. Some things I have noticed from other vertical disks: most disks can self-right if the disk is already spinning when it gets inverted. Few disks can self-right if the disk is stopped - start-up torque isn't the best feature of brushless motors. Disks with surrounds (thinking of the VD series of bots) almost always self-right.

How about adding a pair of HDPE extensions to the top of the disk support arms? I think that with some experimenting you will find a hight where the motor can get the disk up to speed and where the disk has enough engagement with the floor to pop Overdrive back on its wheels. The extensions would weigh very little so its well worth trying.