I moved forward in time a little to make this video about Jingle's visit on Christmas Eve in Animal Crossing City Folk.
The rules with respect to finding Jingle and obtaining more than one gift from him have changed a little from the original Animal Crossing. He now may be found in ANY darkened house as well as anywhere outside. You cannot expect to trick him simply by changing outfits either. You need to use different accessories, which actually adds to the fun. I felt I was playing a Masquerade game along with the 'hide-and-seek' that is part of the encounter with almost any Special Visitor in Animal Crossing.