Some people don't rebound, when hitting rock bottom. Good to see, he gave him a really fair chance. It could be view as patronizing, but adventuring was, what that hero did and he wanted to continue with Dylan. He gave him that recommendation, which is as good as an starter pack. (Though he got himself fired over and over again from those mercenary bands. I worry a bit.) He didn't leave him in the cold. It's a good practice, even if it's just to sleep well yourself.
Now for those magician and saint thots...