I contacted him and he says he mailed his rent check  and it has already been deducted from his account.  

Padsplit is the one not allowing that. 

However, an essential exception emerged in the 1990s, allowing specific rental income to be categorized as non-passive.

HOWEVER, I do not think VRBO and Airbnb do not allow two accounts for the same property, so you have that hurdle to cross.My advice would be to cut ties and move on. 

Here's my question: Do I qualify for a tax deduction considering the substantial loss on the property? 

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Zoning is also a big deal- the piece of land has to allow for multiple units and of a certain size.

You can speed that time frame up by adding more per month this still allows you to keep the rental and speed up the payoff of the home and save interest at the same time.

@Nick Maugeri It also depends on your level of risk tolerance for whether you want to leverage a property and if there are issues with the property that will not allow it to be financed initially.

However, an essential exception emerged in the 1990s, allowing specific rental income to be categorized as non-passive.