Hugo is pretty laid-back so he'd be okay with Harry from any canon-point. Draco is going to feel weird no matter when Harry is from, BUT if Harry is around the same age/older, he'll know about Draco "disappearing" from society for a year and the paper speculating he went "mad" and calling him "madmalfoy". If he is more than a couple of years older, he'll know Draco went to work in schools with anti-bullying messaging. A school counselor more or less.