I've been to Winslow they were hit pretty hard by the economy it seems, I think its nice they have a sign from the song. I don't seen anything wrong with it. Its sort of a musical landmark I guess.
I have been to Winslow, AZ. There is in fact a corner with a cowboy statue and on the wall are murals that are supposed to look like windows, with a girl in a flatbed Ford reflected in them. There was also an actual flatbed Ford parked nearby when I was there. I have pictures, this shit is real. There's also a gift shop across the street where they play an Eagles DVD on an endless loop. When you leave, the employees say "Take it easy!" After all, since they cut off route 66 why else would you stop in Winslow?