I've been getting into this a bit lately, but have not fully committed. I rode about half of the Kentucky Adventure Trail a few weeks ago. I did things on 2 wheels that I'd never attempted before. I was in mud and water above the tops of my wheels with the throttle wide open...riding up steep grades trying to carry speed where the entire trail was covered with rocks the size of softballs...riding down slick muddy hills with zero traction for braking. Some if it was challenging and fun, some was extremely difficult to the point it was risky and not much fun.
I think every experience on 2 wheels will teach you something. That one definitely tested limits.