However, the MLS in San Diego as well as the appraisers I've worked with do.You'll definitely want to check to see how the topic is addressed in the particular locale the property is in. 

Will the cash flow from the new property quickly pay this back?

Hope is a bad strategy.The only on market strategy that I think can work is paying cash/line of credit/hard money for a property that does not qualify for conventional financing.

If you share the city & state where the property is, I’d be happy to connect you with someone specific.

I currently live in Greensboro and own one property I live in that Im planning to rent out once I find the next.

Embarrassingly, I listed our property with the usual $50 pet fee (which can only be $35 now) and asking for income 3x rent (which is now 2x).

I recommend that you find a trusted or recommended Mortgage Loan Originator (MLO), who can give you options for property-based loans (mostly investment loans) and they don't use your taxes but the P&L of the property.

The outcome is on going as I just listed all the properties.

Is the property already zoned multi-family?

Ultimately though, it will depend on the lender and the availability of funds (assistance) available for the demographic area that you are purchasing in.Do you have a property that you are looking at?