You may want to look at what others have done before you to see what worked and what didn't. Since you have the winter to plan, you can look up some of these and see what happened...
Peter Shatalow's 2 hour documentary on Street Theater & Street Performers
"The Street Singer" (PBS 1984)
"Street Art," was an episode of an educational film series from America! created by Louis Schwartzberg of Black Light Films in 1999.
"Street Music" documentary film which focuses on NY street and subway artists by JD Marlow in 2003.
To some, the most significant film on street performing was the 1938 Mayflower Pictures "St. Martin's Lane."
...and of course, the videos here at Busker Central
Good Luck!
