As much as possible, with any type of road, especially the highways and freeways, I set their municipalities as accurately as I can. Sometimes, there is guesswork involved. In these cases, I use existing surrounding streets as a guide to know where the city limits are, and I also look for density of streets to determine where the most likely edge of the city would be. I then usually pick a street which intersects a highway to be the point at which I make sure the city name is entered or cleared out. For freeways, I do usually end up having to add a junction where the limit would be.

If the map overlays displayed municipal borders then it would be an easy matter to do what you suggest...but they don't, so I don't worry about it. I once tried to do it using http://www.usnaviguide.com/zip.htm, but found it far too time consuming.

banished
http://www.tinyurl.com/wazebanished

One of my biggest pet peeves is when a road has so many junctions, so I find myself spending a large amount of time removing junctions. Sometimes a 1 mile stretch of road will switch back and forth between 2 cities because it is the border and I find myself conflicted as to which it should be labelled as or if it should just be blank.

Agreed, I do apply a city name to Interstates if one is available. In rural areas, the interstate may be the only road around so it really helps to define the geometry of the city on the client maps.

If a road dips between two municipalities along a border, it is an annoying pain for sure, but I'd think that (if this theoretical road isn't a freeway) the addresses of the businesses and residences along the road depend on having the right information.