@behindtheurl
Yes, your question makes sense. ??
I have two questions:
1. Did you customize any Theme files? Or just using a Theme out of the box with minimal customization beyond maybe the header logo/site name and some styling?
2. Is all of the actual content appropriate for each (new) site?
The only reason I can see to duplicate (clone) the database is if all or nearly all of the content would be the same for each city…it will save work if you don’t have to recreate what is essentially the same content. If it’s not, and each page would need to be modified anyway, then I’d just install new versions of WP for each city.
If you do duplicate the database, then there are no “files” to change, you could just change the content in one of two ways – manually (if there are not a lot of pages, e.g. just edit each page and change “Chicago” to “Denver”) or if there are a LOT of pages and LOTS of city name references to change, you can just do a SQL query to find and replace those references (backup your db first!) If you’re not comfortable with that, there are plugins that make that simple – add the plugin, type in the old reference and the new, and it combs through your content and makes those changes for you. HOWEVER, it’s still advisable to have someone read through the content to be sure it looks good – you don’t want a site visitor spotting typos or inaccuracies (e.g. a reference to the Great Lakes on a Denver site).
If you haven’t modified or created new template files for the Theme, then you can just upload all of the same Theme files to the new (wp-content/themes) folder for the new or duplicated WP installation. If you DID create or modify theme files, just look through them for any hard-coded references (URLs or citynames).
Then you will just need to make sure logos and site names are correct (check both the Settings>General page and if your Theme has one, Appearance>Customize or Appearance>Options pages).
Take it one step at a time and you should do just fine.
Good luck!