Lorne Richmond: 2 books

Bobby Jones thinks of a crazy idea to catch the muggers that murdered his friend. He would supposedly stagger down the most dangerous street appearing drunk to see if they'd try it on him. He meets a mysterious girl that wears a mask, and goes around the city skating on roller-blades. He starts to fall for her, and pursues this girl. Things get complicated the more he does.

Legend has it there's always at least one human alive that can lead the way through the untried lands. The Great Watcher was promised by the cart pusher he knew the scenic route. Now because a single wrong turn leads to death, and his new strange friends depend upon the bum to overcome the obstacles...