Sword & Sorcery series. Small-time Earth Hustler dies, is transported to new realm. Read 2015-2021. Spoilers ahead.

[Jason]

From I remember the book starts on Earth Hustler makes his last bad deal gets killed ends up meeting the ferryman hustles him to be reborn. He ends up immortal, the world he lands in has magic they mistake his sleight-of-hand as magic
I believe he ends up befriending some Orcs And makes a deal with their Queen about getting gold the human Kingdom owes them
Later He meets up with a traveling entertaining group does a little crime to the magic Guild cuz he can't join then later with the traveling group they do some more crime to a Duke