Same dilemma that LEOs have, with human adversaries, if patrolling alone. I wanted to carry my less-lethal Taser positioned for left-hand use, but the rules required that the Taser be carried (1) cross-draw, (2) on the opposite side of the body from the duty pistol, (3) for strong-hand deployment. I could have argued that I was wearing my duty pistol on my gimpier right side, and that as a left-hander, there was nothing weak about my left hand, but, then, the PD could have responded by scheduling a hearing to determine if I was medically fit for duty. We could, thankfully, carry OC spray at any location, on the belt, that we preferred.
A goal was for one officer to provide lethal cover, while another uses the less-lethal force option. Ideally, a third officer would ready to “go hands,” with handcuffs or other restraints. (I worked for a PD in which patrolling alone was the norm.)
I reckon that your plan for the hippie to lead, with OC spray, would work, while hiking in bear country.
Down here, in swampy SE Texas, it is ‘gators that give us the most scares. I have not read any reports of the efficacy of OC, on reptiles, so, no need to recruit or hire a hippie to carry the less-lethal.