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It's no huge deal to have to back up and to it again,
Observation here....backing up to do it again, probably wont be an option. Remember you are on a city street when accomplishing a "button hook". This is generally a one shot attempt, as traffic will be behind you, impatiently waiting and "pushing" you to get out of the way. Most of the time you gotta get this right the first time.
How do you know when the "jughandle and button hook" are needed comes throught experience with city streets and practice of the manuever, and really important to understand the turning radius of the tractor trailer combo. Position of the tandems will also dictate the turning radius. Another note if the tandems are forward, you have to keep in mind the trailer tail swing, that you dont "swing" it into a hapless 4wheeler coming around your side.