It's got an awkward layout of both units, but is in pretty good shape for the age of the home.What am I missing?

It may be worth it to just block off access for one unit, or split it awkwardly and have it primarily as a "dog run" or garden type area than a true backyard for either tenant, but definitely do away with the common space as soon as finances allow.

What made your meetings awkward?

Save the awkward moment later, and don't hide it now.

It will be awkward if it goes out in those scenarios.  

Not to say I wouldn't considering representing, but I don't think theres a large enough clientele out there that values a socially awkward realtor showing up in a multicolored Accord, ripping cabinets down and chasing roaches around with an air nailer.

Regardless of what happened its going to be an awkward conversation for the tenant to go through, and he will likely get defensive. 

But it's still awkward to start the conversation. 

I am in a awkward position, since I have my license with him.  

I didn't end up buying that one for unrelated reasons but.....AWKWARD!