Technology wise, aircraft are already 90+% automated - autopilot does basically the whole cruise phase, pilots are there to do the communication with ATC, manage the autopilot, and be hands on for taxi, takeoff and landing.

From a legal/policy perspective, the aviation industry is held to a much higher standard of reliability and safety than the automotive industry - the AI driven YOLO that companies like Waymo get away with. It's not just that autopilot systems have to always work, it's that they have to always behave in a predictable way.

Pilot here.
There's already a huge amount of automation available for airplanes large and small. The current top of the line will allow the airplane to connect every phase of flight except for the takeoff, coming all the way down to landing on the runway. In your average airline flight, probably 80 to 95% of the flight is flown by computer. The pilots are managing the aircraft, talking to ATC, etc. So you could argue that that is already there.

If you mean the ability to conduct a trip without an operator, IE little girl jumps in the back of the car and says 'Tessie take me to school!' and the car drives her to school, that will absolutely happen in cars before airplanes. The simple reason is edge cases and emergencies. In a car, if something goes wrong, you simply pull over. Or, worst case scenario, just slow down and stop. It's not great but it's not terrible. If something goes wrong in an airplane, you need to keep operating the airplane for anywhere between 10 minutes and 4 hours including a landing. A lot of what pilots do in emergencies is figure out exactly how their airplane has been damaged and strategize around that. A lot of that is intuition, the rest is deduction based on understanding of how the airplane works. Since the computer can't see out the window or feel things like buffets and sound, a computer won't necessarily be as good at that. So the pilots aren't going anywhere.

I think truck driving is probably the next thing. There's laws (at least in the US) about how long a driver can run without rest, long haul routes are generally not very crowded with traffic nor complicated. If you can get twice as many hours out of a robot than a human, you can recoup the investment pretty quickly. I could see a hub-and-spoke model where robots handle the long spots with humans taking the busier spokes.

By tradition, the automobile industry is allowed to build machines that kill people.

The airplane industry isn't.

less variables on a runway. its a very strictly controlled environment unlike most roads

Airplanes, though I suspect they will never be truly without someone to assist in case of emergency.

Cars have to contend with a number of random obstacles and unique challenges. Planes have defined runways and taxiways and, via autopilot and GPS, their flight paths are relatively easily defined and controlled.

The sky over one city is pretty much like any other. Main Street not so much.

Am I crazy? There are already self-driving cars, aren't there?

Airplanes will never be pilotless, there will always be a human in the loop for redundancy. A failure in a self driving car could kill a few people at most, a failure in a pilotless plane could kill thousands.