Hmmm...

Anakin was a skilled pilot when Obi-Wan met him, so maybe something could happen that would require Obi-Wan to go somewhere and need a pilot, resulting in Anakin getting caught up in something, leading Obi-Wan to begin training Anakin somehow... I don't know. Maybe you could go somewhere with that, but you'll have to think of something that would force Obi-Wan to go off somewhere and that he would need a skilled pilot for.

Good luck, I'll share any thoughts I have as they come but right now that was the best I could come up with. :)