I think Voodooo doll has some good ideas, but I know I'd never ever ever never ever go around the block in cosplay. Cosplay goes from house to car to event, and that's it for me. Maybe a drive-through or something, but that's it until I get to the convention. Being alone in costume is far more nerve wracking than being among fellow cosplayers.
Smaller conventions and photoshoots are the best way to go.
Add me on Skype to join CosCom chat group
Izaya (Durarara) - Complete
Drossel Kainz (Kuroshitsuji) - 90% (need new wig)
Judal (Magi Labyrinth of Magic) - 15% (shirting)
Sheik (LoZ/SSBB) - 10% (armoring)
summer!Jack Frost (RotG) - 10% (wigging)
AAC Summer Matsuri
Another Anime Convention