The word "pilot", especially in the SW universe can mean more than just flying in space or hundreds of feet or more above ground. In our world the term is also used for ships at sea, and that was even it's original meaning before planes were around. Podracing was indeed referred in the context of the movie as piloting. Although not necessarily very high above ground, it was piloting. Regardless of how accidental Anakin destroying the droid control ship seemed, I believe the force was guiding him even unbeknownst to him, remember how Qui-Gon said "Nothing happens by accident." Regardless of how he did it, Obi-Wan knew both these facts, so why in the heck would he not have thought Anakin was already a great pilot, especially for his age? He wasn't even on autopilot for the the second part of the trip.
1 a: one employed to steer a ship : helmsman b: a person who is qualified and usually licensed to conduct a ship into and out of a port or in specified waters c: a person who flies or is qualified to fly an aircraft or spacecraft2: guide, leader3: cowcatcher4: a piece that guides a tool or machine part5: a television show produced and filmed or taped as a sample of a proposed series6: pilot light 2
A lot of Kenobi's OT statements were vague and gave no details, leaving it all open for some wiggle room. This comes from hearing these statements for years and assuming they mean Anakin as an adult, when they don't specify his age or circumstances. When they seemed to contradict what we had in our imaginations, some screamed contradiction. I doubt anyone new to SW would have this problem if they watch the films 1 thru 6 for the first time because they didn't have all that time to fill in the blanks based on the vague Kenobi OT statements.
But as said above, enough on the prequels.