I decided since the arena was still a little rough and the ground in the field was still a little slick, and since Bobby doesn't know how to use his feet sometimes, I'd give him phase one of the future eventer test: trail riding by himself. And he totally passed; he was such a good boy!
I took him on the road, the grass on the side, and off into the gamelands a little. He had no problem going up and down the steep sides of the road to get from one place to another and he scrambled up a pretty steep, really narrow deer path like a pro. His only little naughtiness was when a car passed us in the other lane and a truck pulled out of the driveway in front of us at the same time. I had asked him to stand still so the truck could pull out and he spun around slowly when it did, but he turned right back around and went on with no problem. He was a little snorty when he heard what sounded like really big dogs barking, but he turned off onto the gamelands trail and totally ignored them.
He was so relaxed, and he kept his ears forward or turned back towards me, and even walking back to the barn he wasn't rushing or anything. Now I'm a little more optimistic about taking him schooling, and on the eventing picture as a whole.