If it would cost a certain amount of money and time to advertise and show new potential applicants, you can offer to deduct that amount from the tenant's full liability and see what the response is.Hope that all makes sense.

I do see the plus sides of the property tax deductions and interest deductions,but I was wanting this to cash flow much better.

I assumed you were talking about regular Social Security benefits.ROTH withdrawals are tax-free (if requirements are met) so should not affect taxable income or capital gains rate.Rental losses can potentially decrease taxable income if you can deduct them (income needs to be less than $100K/up to $25K of losses can be deducted).

"From what I've been able to find, I understand that if I make a portion of the mortgage payment, I am entitled to a proportional portion of any personal deductions (e.g. the mortgage interest deduction)."

But  you will face other problems because your interest rate deduction won't be available for duplex  so consult CPA.I would rather cash out from duplex payoff HELOC and keep business separate.

The property generated gre​at monthly cash flow and yearly deductions.

Deductible: This is not a coverage but rather your portion of a claim.

They give the impression that if property tax is being levied...if it is a taxable PIN, then it must be a piece of property with value.

All I had was passive income, and I cannot deduct it from the schedule E as it's not a rental expense.

Took 2nd Mortgage out at beginning to Pay outstanding CC Bills Ect, Justified paying because Tax deductions on Mortgage.