Then build and understand the financial model around that, that will automatically define the neighborhood and the building type for you. 

I'm not a fan of giving my financial information to random companies.... 

As you're seeing, of course, things outside anybody's control can impact this - and Hawaii also has the potential to get affected by hurricanes, on the natural-disaster front.  

They could still get the bonus if they spotted me on the mortgage payments, but they pulled back because they assumed the worst of financial troubles.

With what you describe, it doesn't sound like your wife is completely against mortgages and debt, it just sounds like that paid off property is and asset in your family's financial 'toolbelt' so to speak that she takes a sense of security in knowing is paid for. 

Not only can you save 10% of gross rent but you have better control over repair decisions and you can defer non emergency ones based on your financial situation.

I think buy and hold is the best route to long-term financial freedom.

The duplex makes better financial sense. 

In other words, if we do a 50/50 split on equity, and things turn south for whatever reason, I am taking on 100% of the financial risk. 

Every financial planner....and I mean every single one....will advise that you absolutely need to have 3-6 months saved for an emergency fund.