Larry, there truly are ways to greatly speed up the learning curve for safe autopilot driving. The first step would be to drive on a road without much traffic and practice taking control from the autopilot. You use the twist of the steering wheel, pushing the brake, and pushing the button on the end of the autopilot stalk. What this teaches the driver is that the autopilot is only going to be driving until that half-second when you're not so happy with its driving, and then you click it off. Next, you show the driver examples of challenges that will exceed the autopilot's ability to perform satisfactorily. You drive on a road with poor lane edge markings and either see the autopilot turn control over to you or steer in an unsatisfactory fashion. Then you take a turn at a very exact slow speed which nonetheless exceeds the autopilot's ability to execute the turn. You brief the driver that he or she will have to take over at some point during the turn. Through these simple exercises, you demonstrate that the driver is indeed in control of the outcome of the drive at all times and that sometimes there's a need to say "not good enough" to the autopilot and take over.
The next step is to teach the driver to evaluate the performance of the autopilot, based upon the conditions. On a scale of 1 to 10, how is the autopilot performing? At what number do you take over manually? You then give the driver a chance to drive a road that has some autopilot challenges such as too steep a curve, poor markings, glare, or construction zone. You ask the driver to as soon as possible tell you about the threat to autopilot that lies ahead (and thereby train the driver to use some of the free driver's brain bandwidth to anticipate problems before they become obvious). The driver gets practice taking over, and if the driver doesn't take over soon enough, the instructor (as was properly briefed ahead of time) says "take over." Thus, in a controlled environment that challenges the current autopilot technology, the driver becomes confident You present the driver with a road that is totally unsuitable for autopilot usage and you brief ahead that if encountering such a road, the student is to turn off the autopilot and say, "unsuitable road."
In flying, we would never expect the student to just learn from their own mistakes. We challenge them and give them the ability to fly safely in the marginal situations and to avoid situations that are worse than a certain level. The same type of training can be given to autopilot drivers. Inexpensive simulators could be created if training in real Teslas becomes too scary. The goal, though, is to show the new driver what the marginal situations look like, how the autopilot performs in such situations, and how to be comfortable taking over.