This last screenshot of the 404 page that has a Local icon indicates that Local’s router is working, but that it doesn’t know where to send the request to. That means that for some reason the individual site isn’t being created correctly, or isn’t being registered correctly.
Can you try creating a new, plain WordPress site? If you still have issues after creating that site, can you please provide your Local Log? See this Community Forum post for instructions on how to do so: