I think that's because your appearance is below 6 when I restarted the game and my appearance was 5 no matter how much I rested at the track he didn't appear, and I even got to go in the wagon to buy some shit so I came to the conclusion you need to have at least 6 appearance
I've listed some places you get to talk with him in one of the comments down below you could read that and see if it's useful if not just ask again and I'll try to help(if you don't want to go looking through the comments just click on my profile)
