Dean's Place reminds me about a story I once heard about a family that travelled to France and stayed at an old tavern for a night that was decorated as if it was the turn of the century. A year later they went back and couldn't find it again. They arsked the local's about it and discoverd that it had burned down in the late 1800's.
1/ Perhaps the doorframe was moved and reused. The door is still linked to the bar for those that know how to step through it the right way. Or if they knock in tune to a old song before opening the door?
2/ Mac's bar is designed to help stop magic effects in the Dresdenverse. Dean's bar could flood the area so no other magic but Dean's could work. The T.V. might work on the local day if the antenna was somehow linked to the outside. Perhaps the T.V. is in an antique store gathering dust in the local timeline?
3/ The barkeep and staff could just mindblank the odd money and clothing by seeing it as the normal everyday clothing of there time. I.E. Instead of seeing a man in a biker jacket and motor helmet. They see someone in a tweed jacket, trousers and felt hat with the money of the time they are from.
I have never played in a FATE system but if you can think of an interesting place to set a scene in. Sometimes the face it can't be explained easliy is a good way of getting the players into the story/game your running.
Hope that helps you Harlan Quinn.