What is the best way to create a set of rooms that mirror a street or road? Should I create a room for each "section of the road" or create a single room?
If it is best to create a single room how do I return the Player to the correct room that they were last in?

I would do a single room for each section. A n-s section of road with maybe four entrance on each section - ne, nw, se, sw. If you try one room with several exits off the road, you need to customize your exits - grocery, home, arcade, etc. if you do one road room with custom exits, you can have an 'exit' command exit and move that player back to the one road room. Make sense?

Yes, thank you.

Depends on what you plan doing for your game and the meaning of the given street.

If you somehow plans using it as a tactical space, for a firefight, for example, then divide the street by sections would be interesting.

If you plan using it as a narrative space, than it only matters what narrative you are building up and what is the dramatic mean of the given street.

Let's say, as example, you just want to build the street because of the various shops and characters to be found there. The street would be a single Object / room with all other elements orbiting it.

At other hand, if you plan a character advancing through the street and having places to hide, shots to duck and enemies to defeat, each piece of the street will be a different stage towards the objective.

When writing interactive fiction, perhaps attempts only mimicking actual places is not the best, but you should find the meaning or purpose of this place in your narrative.

Deckrect's post sums it up really well. Players are rarely going to enjoy bouncing around in big empty spaces. You're going to want most rooms to exist for a purpose. If the only thing the road needs to do is be a transition from one location to another, a single 'room' can represent miles and miles.

I'd only break it into sections if each one conveyed something about the story, or was part of a puzzle...or directly connected to a more important room, but even that only on a case by case basis. Sometimes it may make more sense to just send them directly to where they need to be for the story to progress.

I have used a single room as a road, using ' first time' messages on the foreward exit to find an object in the road. Going back is fixed by an exit to nowhere displaying a message about the futility of retracing your steps ( impending night) this means the same general scenery objects are always there, but can be added to as discovered using repeating first time messages. A crude way of doing things but it works for me.