A John is a bum.  Much like the stereotype, he lives near this sort of transportation infrastructure. Where does he live? - bus depot - beach - train station - bridge - bridge  The best answer is
bridge

Sam didn't like the people he met while traveling.  What might he do to get away from them? - come home - airplane - learn from each other - go out - make art  The best answer is
come home

Where would you write down a passage? - labyrinth - bible - hotel - diary - journal  The best answer is
diary

What can happen to money after buying too much beer? - intoxication - boredom - problems - pleasure - get arrested  The best answer is
problems