I've always played a game with my daughters while we rode these trails. I would tell them to pretend I was hurt and they had to find their own way on the trail. So I would put them up front and let them take turns finding the trail makers so they knew they were going the right way. It helped them to develop an eye to notice subtle trail markings.
Years ago I encountered some folks from Michigan out west elk hunting. They asked us for direction to reach the area where they had camped. I was heading that general direction and told them they could follow me. We rode 5-6 miles till I had to turn off and head toward my camp. I told them to continue following the trail markings and it would take them to their camp. They both quickly responded "What trail markers". I asked if they had not noticed any of the marks we had passed. I had been watching for blazes on trees, rock cairnes etc. They of course had not. Since then it was important to me that my daughters know how to spot the official trail marks. If they ever got lost, they should have some idea of how to get out of the mountains. Every summer we have folks lost in the wilderness, Often with tragic results.
Makoda, I've never rode that trail that you did. We have often started at the Highline by Mirror Lake and rode into Naturalist Basin and Four Lakes Basin. We often ride up The East fork of the Bear or start at Christmas Meadows and ride up the Stillwater fork to the Cirques at the upper end of the drainage.
I have also rode in from Moon Lake and Swift Creek trail heads as well as most of the North Slope trail heads into Red Castle, Henry's Fork and Brownie Lake .
My daughters still enjoy camping and trail riding, One even called up from College, saying they had a long weekend and would I take her and her room mates for a pack in camp on the horses. We loaded up and went up to the Yellowstone area. The girls had a great time
My daughter in the middle with her two room mates