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A sad thing to assume but it seems like something that would be the writer's style.
Alternatively, he could change his primary job to something that wouldn't raise suspicion and take the portal from the neighboring town again. IDK there are a lot of things he could be doing with his abilities but instead of it being plot holes I think he's just not great at thinking on his feet (as evidenced by Roxanne having to be the one who suggested they use warp to get into the labyrinth to skip out on entrance fees)