OpenStreetMap doesn’t have a concept of “streets”, it only has Way records which are sections of roads. A street may be composed of one or more Way records. I have to piece these Way together within CityStrides to produce the full Street. I do that by matching them on their name.
If a city has two streets with the same name, CityStrides joins them as one street. I don’t currently have a workaround/fix for this.
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Why would a city have two streets with the same name?! 
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Good that you say that. I found it odd the first time then I learnt to live with it. For Sweden, citystrides uses a “higher” administrative level called a kommun (or municipality in english). In a kommun, then you find the main city, that takes the name of the kommun but also smaller towns/villages. In essence a kommun is built of villages and these villages can have the same name. Running the entire length of a street and not completing it because the name is similar in other villages within the same kommun no longer bothers me because I know that I will run on those sections as well. These villages also differ by post code but this is cumbersome to factor in and probably would make the code buggy.
“Why would a city have two streets with the same name?!”
An example here in Omaha. Nebraska is “Park Road”. Several city parks name their entrance roads or circulation roads as “Park Road”. They are functionally independent, and in different parts of the city, but that’s what OpenStreetMap has for the name, so they get considered as pieces of the same street in CityStrides.
…doug