You will have to bear with me, I haven't read this these books since high-school. That being said I am looking for a fantasy book series about a boy who is unaware of a different realm that he travels to then at the behest of the grand wizard there asks him to join a quest to head to a mountain and slay a dragon and claim the score of a life time. I keep thinking wizard's apprentice meets Hobbit.
The boy lives in the inn with his mother and stepfather then step father is horrible to him so he runs off to get away when he finds a building that looks out of place he's curios and goes when he meet the wizard that offers him apprenticeship and adventure. Oh and something that always stuck with me is the messengers in the book they look like bowling pins and they show up where and when ever and head butt you until you pay them.
I read the book I'm guessing around the 2013 to 2014 mark and I remember the book series not being completed at the time if that helps.