Saw this exchange on the investing forum under a thread debating whether or not to payoff a mortgage early...
"Don't forget that your mortgage interest is tax deductible, so that's another advantage of having the mortgage there."
Biscuitwhomper - "True for many, but not me. My expenses are not enough to surpass the standard deduction for my family."
In my county, property tax bills come out in October of say 2014, but aren't due until January 31st of the following year (2015). About 6 years ago, I inadvertently paid the taxes in January at the last minute. When I was talking to an accountant friend, he informed me that I couldn't deduct those against my 2014 income (duh!)..
BUT, what you can do is "double up" in 2015. So if your family or individual return has itemized deductions below the standard deduction it could be beneficial to "double up" every other year. That's what I've done ever since stumbling across this.
Example.. let's say your property taxes are $5k per year and mortgage interest is $5k per year, and you have no other deductions. You're below the standard deduction for a family ($12,600 in 2014), so you just take it. But alternate every other year on the property taxes and every other year you have $15,000 in itemized deductions (two years of property tax at $5k and $5k of interest). So in this scenario, you'd have $2,400 of extra deductions simply by choosing which month you pay your bill in...
To double up - pay the 2014 property tax bill in January 2015, and pay the 2015 property tax bill in December of 2015.
*** I'm not an accountant, full disclaimer. Hopefully one that is will chime in.
Granted the numbers and the strategy won't necessarily work for everyone, but for those who pay their taxes on their own (don't escrow them), and are just below the standard deduction, I think it can be of help!