You will find the most help by obtaining a topographic site plan that shows the contours of the area you want to model. You indicate that you are attempting to create a small city and this implies that the site is fictional, in which case you can create an imaginary sloped urban site from which your model may be derived.
If you decide to use the same site as the Fat Pencil Studio study, it may be possible to get that information from the Seattle Department of Public Works. You will need the latitude/longitude geo-reference data or general elevation data to assist in recording the site data. After the actual site has been identified, it may be obtained through Google Earth where you can import the terrain information and drape the site plan over that. There are a few videos on this subject available on the YouTube channel. Several examples are found at the following urls:
Go to the Extension Warehouse and look for Eneroth Upright Extruder. That plugin and Follow Me and Keep are intended to take a profile, like your curb-road-tram track, and extrude it along a sloping, twisted path.