Could I use a jack caster wheel to solve this problem?

Using a ball with a 5 inch riser worked but in the end I found it stressful to change the ball in the middle of the street. As for the boards, I have an angle to take into account; I’m not good enough to backup directly on the boards in these conditions. So the best solution is to have Air bags installed on my truck and this will solve the problem.

Thank you all for your great advice.