Ok, so I've done a lot of thinking about this and I'm pretty sure I got this figured out. Given two different setups:
1) 150 kv motor, geared 24:36 with 83mm wheels, 6s LiFePo, theoretical top speed of 19.2 mph
2) 300 kv motor, geared 12:36 with 83mm wheels, 6s LiFePo, theoreitcal top speed of...