/lit/ - Literature

/lit/, I'm looking desperately for a high-fantasy book that I cannot, CANNOT recall. I can bring up a few points...

1) The main characters name starts with K.
2) The first book goes from the future (Where he runs a tavern and has no powers), to the past, showing his rise to power (In a magic school, exploring the world.)
3) There's a part where he gets sucked into a dream world by a dryad or something, and she bangs the hell out of him and then gives him a badass star cloak.
4) In the future-ish part, there are these black spider-like metallic (?) creatures that attack people.
5) Also, he's some kind of amazing, insane hero that people talk about constantly.

Please help me find this series! Thank you!!