Don’t try to mix them into one person, I think you are eliminating a lot of great advisors on both sides in that case.

Sweat equity will reduce or possibly eliminate the negative cash flow. 

On top of the 6 months only for the subject home, you now need 2%, 4% or 6% of the aggregate unpaid loan balance and 2 months PITI for your primary and second home This can be eliminated as well if your primary or second home isn’t the subject property.

I have zero debt of any kind.

The bank that gave us this commercial loan looks at the debt-service cover ratio (DSCR) and didn't care that the down payment was a gift from a family member.

Does the negative balance indicate that there is a unpaid taxes debt to the county (meaning, if I see debt in the county account it should be referring to the same debt)?

Or, they are not telling you about the other predictions that did not work out as planned.If you are really worried about a market, use less debt.

As of right now we are heavily focused on being debt free so we are limited with cash.

The only debt I have is my car loan. 

I have zero consumer debt and no car payments, as I have a company vehicle.1.