I have great credit score and no debt but it seems tough to get an adequate DTI in the LA/OC areas. 

Property needs a new AC and natural gas furnace.

We've gone to All Natural Stone in Berkeley and Granite Expo in Emeryville.

When you GET IN and consume knowledge on a dedicated persistent path, success is a natural outcome. 

We even talk about plans to move here one day after falling in love with the access to nature and how nice everyone seems to be. 

Most likely the state where the property is located is where lawsuits would be brought if they are something for personal injury like a trip and fall or something of that nature because the “cause of action” arose in that state.

My concern is that I am unsure he is going to be able to land another high five/low six figure job in the near future given the nature of what he does. 

The big advantage of buying a condo is the maintenance free nature of it, but if the people responsible for handling the obligation of collecting the money and managing the association are compromised it will have a necessarily negative impact on your investment.  

I am 60, and would like to generate adequate income to cover retirement within the next 10 years of real estate investing.

At this time, based upon my research, I am not 100% certain they would approve my plans for an ADU since my property is located on a hillside without adequate parking.