Right, you would likely pop a tire on your friendly neighborhood pothole. Even if you were lucky and avoided all of that, the tires will bulge in the center, drastically reducing the contact patch with the ground and you’d have probably 15-35% traction compared to proper inflation.
Yes, Portland had decriminalized public nudity if participating in a peaceful protest, while not engaging in sexual conduct, and away from certain restricted areas like parks and schools. The annual naked bike ride is an organized peaceful protest that chooses its route appropriately as to not encroach on any areas where public nudity would otherwise be prohibited.