Perhaps try to find a non-conforming duplex or a house with a separate entrance, where you can build out.

I have city inspector requiring that I have 60 minute fire rated doors installed on the entrance of two units that are inside our property.

they maintain some of the entrances.

the owner argument is, that's prime location, however, the building will need work, and the layout is not 100% functional (25% is a second floor unit, no a real separate entrance.

I am aware that there would be HoA elements to this approach but am wondering if this is an lower entrance opportunity to this market. 

RH zoning mandates that each "unit" has a front facing entrance. 

It has a separate entrance to a rental unit already (high on our want list), and the property is a sanctuary with stream.

They both have their own entrance, kitchen, and laundry. 

Back when I was 16 years old, I had a business called Travel Aid for Cedar Point visitors in which I provided detailed instructions on how to bypass the main entrance and use alternative routes, which included the chaussee!

It also has potential to become a house hack situation once the basement is fully renovated (new laminate flooring, separate entrance built in, and half bath made into a full bath).