I guess I am a skeptic that thinks between the deductible and the claim fighting that I won't ever get any benefit from the insurance itself.

For instance if you make more than 110,000 AGI or adjusted gross income you can no longer write off your mortgage insurance as a deduction based on current IRS guidelines.

                     $220 Vacancy/minor repairs/maintenance                    $220 a month for water/sewer/trash/landscape/snow (actual should be way less)                     $1000 debt serviceNET loss of $160 a month      The cash flow is terrible of course, but that is mainly from the outsized taxes which was from what I can tell from tax records an extra school levy, total taxes for 2016 were  $2341 on same valuation.

I have done exactly that in the past year.The IRS is specific in terms of business deductions: you have to show that you are in business to make money - so that the IRS can tax you on the profits.

Also, important to know the implications of what and when interest can be deducted.

Every Landlords Tax Deduction Guide.

I plan to qualify as a business and meet the criteria for the home office deduction.

Don't rationalize any numbers, or use anything other than cash (i.e. equity, appreciated gain, tax deductions, ...) since those other items are NOT CASH.3 - If you have a negative number, that means you get more cash back in your deal, within the first year, than you spent (so in this case...used)...and you have a winner.4 - If you have a positive number, that means you have spent money to buy this property...your money.5 - If you fall into the #3 category, you have recovered all your initial cash (seed money).  

. :)@Levi T. the LP raise was 2.1 million.

Deferring your business debt works because it allows another party to pay the debt (your renter), you keep the tax deduction (the interest that is paid), and you gain more cash flow.