Regardless of version, you may:
1) Create the individual road paths with the assumed width, group them, and apply New Stroke to the Group through the Appearance palette flyout so you have two strokes, then widen the lower one and change its colour to create the black border at group level;
2) DirectSelect each of the paths and Ctrl/Cmd+C+F+X+F to bring them to the front and use the Path Type Tool to name them, setting the Baseline Shift for the first one; you may group them.
With this, you are able to subsequently:
3) Edit the roads by dragging over the relevant Anchor Points with the Direct Selection Tool and moving them;
4) Edit the names with the Path Type Tool, just click on the Type and add/change.
Jacob: but unless the grouped roads abutt exactly, they're still above/below each other and will be visibly so, and you can't adjust the type and road paths with their handles both at once. the type paths seems to move differently when you drag over handles too; the type path moves wholly, the road path moves the handle alone.]
i've been playing with this for a while... slow work day
I always find it best when doing maps like this to have the text on a separate layer.
Copy the road paths to a new layer and use them for Type on a Path.
Adjust the type’s vertical positioning on the path by using Baseline Shift with a minus value.
You can drag type along a path by its handle.
With Butt Caps, the strokes of the branch roads will always end inside the through road (if their end points are placed on top of the through road path (Smart Guides say path). And with the second stroke applied at group level it just follows the outer shape as shown in the first OP image. If you hide the Type paths, you can also add new roads and drag them into the basic path group, then create a Type path from a copy.
You can move matching Anchor Points about together.
Adjusting the corresponding Handles is more tricky, but you can:
5) Lock the Type path (group) and drag the Handle of the Road path to the desired position and unlock the Type path (group);
6) Drag over both Anchor Points then drag the Type path Handle to coincide with the Road path Handle (Smart Guides say handle when you are there).
You will probably have to repeat 6) once or maybe twice or more, but it gets easier the closer you are.
Edit: Hi Steve. No frost at night, so I have just stopped carrying our new star magnolia inside every night; now it has a temporary fence to keep the roe deer outside snapping distance.