Noobtown5 books in series
The Mayor of Noobtown Publisher's Summary
It could be worse. You could be stuck with a literal shoulder demon.
After dying and being reborn into a world that's built like a video game, Jim has found himself stuck in a very old-world style new-player zone for low-level adventurers. Unfortunately, the zone fell out of use centuries ago, and no one told the monsters they were supposed to take it easy on the Noobs. Even worse, the only new player around is Jim.
Jim has been given an opportunity, and he'll do his best to take advantage of it.