I guess the biggest problems will be the legal framework and the power of unions. Technically flying a plane should be easier for a computer than driving a car.
Where a computer fails is when judgment is required. For example, you have an in-air emergency, and are going to have to crash land. What do you pick to crash land on to?
Consider Captain Sully's recent decisions in just such an emergency.
Being a private pilot with a lapsed license, I can't possibly see that emergency landing area selection is a problem worse than navigating a street vehicle in an urban environment. Taking all the GIS databases around, I can't imagine emergency landing site selection would be a huge roadblock.
Consider Captain Sully's recent decisions in just such an emergency.