Thanks for the suggestions guys, but it's a done deal. The gravel pad didn't present much resistance (the tire was half flat as well, so maybe provided a better "skid plate"), and the ramp and trailer track were fairly smooth. I aired up the tire coming off, which put a bit more torque (larger rolling radius) on the drum so it did roll off OK. We needed the arm workout on the come-along as well, so all good.
