I think autopathing should be looked into more closely and redone. From analysis, i think autopathing was done while everything in the map was still empty, no npcs, no monsters, no rocks and no obstacles. That is why it looks so unnatural.
Thinking differently, it would be logical to be directionally challenged and a poor driver if your training or sailing level is at beginner level, but gaining mastery, you should be able to drive better. Better in a sense that you do not drive into a horde of gahaz bandits or kagtum nor get stuck from a passing deer or weasel, you also do not sail willing on rocky coastal shores and get beached. getting to master level would mean having better driving/sailing skills that gets you to your destination without hassle and faster, no more passing through kagtum blockades when going to eilton from duvencrune, no more passing through gahaz bandit traps, no more getting stuck at a passing weasel. You simply jump to avoid or skillfully evade traps if you must pass through these hazards.
wagon driving should also be improved, instead of having a totally suicidal wagon, there is an invention called brakes. If the road is too narrow for a turn, the wagon should move forward until there is enough space to turn instead of just flying off the cliff the horses should be smarter than the driver attempt to stop instead of willing jumping off to their deaths (well they dont really die just your wagon). The turning ratio of the wagon is so inconsistent that it can do a 180 degree turn at high speed while at low speed you can only do 20-30 degree turns.
I think reaching guru you get 50% damage reduction when autopathing is active. Also maybe have a 1% reduction on stamina/power/ration consumption for every mastery level starting from skilled 1.