I hope it's all of tee above, so long as you are famous enough. An official won't make speeches about a common theft from the marketplace from a no-name, but as you're fame increases and the severity of you're crimes grow then an official would take notice of you and act accordingly. I just hope you are able to go about you're business even whole being wanted, guards shouldn't be mind readers and memorize every wanted criminal in Skyrim. I think the entire system needs an overhaul, gate guards might notice more than a city patrol guard in terms of faces, but only if the word of the crime you committed has time to travel to another town. Killing a civilian on one side of the map, and then riding Puff the magic dragon to the other shouldn't make it possible for the guards to know of the crime. Have a set/variable time on the spreading of the crime based on location, witnesses, fame, and severity of the crime.
Make each position of guard specialize in his own area, the gate guard will have an easier time recognizing wanted criminals foreign to the city, than a city patrol guard who is more informed about crimes that happen within the walls of the city. Not to say that all of the guards should be dunces to any crime not within their parameters, simply that a guard will not have heard of a minor crime if it is outside of their area. An apple being stolen may attract the attention of the city patrol, but the gate keeper may be oblivious to the action.