I know that when we are new to this business, we are hesitant to spend more money than we think is necessary, after all, we have spent a ton of money on the rental home and getting it ready to rent out, so to think of anything else like a financial software program, is just not on the list of things to do, at least for now.

If you want to just build wealth, love your job, and have a strong financial base and could hold them through a downturn--I would just keep the properties.

I suggest putting together a packet/portfolio of your financial history that shows your smart financial desicions to present to potential leaders.

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.... 

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.