The only way we learned this was from actually talking to him.

But post locally for this and ask what service providers other investors are using.

Most "cash flow" properties are high risk investments that can be underwritten to show cash flow, but actually hold high levels of tenant risk, turn over risk, Capex risk, and only show more cash flow by underwriting with the same assumptions as a high end area.  

However, they requested to do a second appraisal because it was actually zoned as a SFH.

You could use a debt-service coverage ratio (investor cashflow) loan to get around the income needed, but would require that downpayment minimum still.

Most office building inside the city is actually ..... half empty.

In the coldest days in the winter the heat in the units never actually reaches what the thermostat is set to even set to say 65degrees.

once you actually identify a specific property, you need real numbers.in a duplex you may have two of everything (unless some utilities are shared) - two furnaces, two water heaters, two sets of appliances, lots of bathrooms. 

Use a trustee service provider?

Could you give me more information about your company and services?