The AI does indeed "teach" players new positions randomly.
I recently got an email - "Paul Valentino has made noteable progress at his new position, 2B. I'd rate his skills as 60 now." I scratched my head. I didn't remember the player's name and certainly didn't remember putting him at a new position to learn. (Like others, I don't let the AI manage my minor leagues. I do it all myself, including setting all lineups and changing them frequently.) So I scanned through my AAA, AA and A rosters. I couldn't find Paul Valentino. Finally I found him. Lo and behold, Paul Valentino was on the DL. He had been for several weeks. So he actually learned his new position (2B) while his was on the DL!
I don't mind that this happens occasionally I think it's nice to have random "learning" going in the minors. I just told myself that while he was on the DL Paul Valentino was working out with one of his AA coaches who was teaching him to play 2B on the side.
