Are these kosher?

You need to see if you received a benefit from the taxes paid in the previous year that were refunded. If you don't itemized, then you don't get a benefit from the deduction so the refund isn't taxable. It sounds like you don't benefit from the state income tax paid as a deduction. Otherwise, the IRS would send you a notice. The fact that you "rollover" the overpayment is irrelevant.

Alimony hasn't been an itemized deduction in years. It is an adjustment to gross income. That means if you paid $100 in alimony, your taxable income is already $100 less regardless of your itemized or standard deduction. I believe you should gather up your income tax information for 2009, 2010, and 2011 and take it all to a tax professional. If you are already using a "professional" tax preparer, find a better one.

Prepaying your state income tax will only generate income with the overpayment for the first year. You can't deduct real estate taxes unless you had a liability for them so that won't help you either. You can make charitable contributions anytime you please so that part is okay. If your automobile excise tax isn't based on the value of the automobile, then it isn't deductible at all.

Taking income just to pay some deductible expenses is rarely a profitable move. If your total deductions each year are $500 less than your standard deduction, you are already ahead. Taking $5,000 of income to get $4,500 more in deduction would INCREASE your taxable income by $500.

You may be thinking: "but I've done that and never got a notice from the IRS so it must be legit" WRONG! That logic is just like sticking a piece of jewelry into your pocket and walking out of the store. Just because a security guard didn't catch you doesn't mean it's legal.

I hope this helps. Gary

===============Kosher #2. - Way back in 1972, I started paying alimony. Back then, alimony was a deduction for schedule A. Since then, I've bought a house, so I've never even looked at the standard deduction. Until now. Now, I have no mortgage interest anymore. I just realized that my deductions are not that much more than the standard deduction (including my over-65 bonus). All state withholding is currently optional (from my IRA/401, etc.) or with quarterly payments. I am not employed.

Am I allowed to do this: In late December, 2012, take an extra $15,000 from my IRA. Thence, prepay as much as two years' worth of state income tax. Thence, prepay 2013 real estate tax. Make 2013 charity gifts in 2012. Borrow, if necessary. Take all those deductions on my 2012 federal return. Thence, hold off filing my 2012 state return until January, 2014 so I don't get the refund in 2013. If I play my cards right, I can postpone everything except my automobile excise tax ($400) until 2014. When I file my 2013 federal return, I take the standard deduction. ===============No. and accounting method isn't a factor here for most items.

One cannot prepay more than one year's worth of real estate tax. As most bills for tax at the county level are July-June fiscal years, you only have 6 months that you could pre-pay at most due to tax year overlap. Beyond that, real estate taxes have not been determined, and therefore are not incurred.

All charitable deductions must be in the year in which the gift was made or completed.

Delaying your state income tax return beyond October 15 means it will be late and some states penalize late returns regardless of any refund it may generate. An accrual-basis taxpayer would be unaffected by this action.

Agreed, 6 months out, but, my Nov 1st bill can be paid at a cost of 2 month's penalty or 3%, to get pushed into next year, so even years he can have 9 quarters paid, odd years one quarter.

For charities, one can make all contributions in the even years, in January and December. The charities that are fiscal July-June will consider him an annual donor, those on calendar, a twice year donor every other year. Regardless, he can fell he's donating annually, even if it's otherwise for tax purposes.

For some, the Real Estate and Charity loading can be quite the tax savings every other year.

On 2012-10-16 13:53, NadCixelsyd wrote: [...]

No.

As contributor Katie J. has stated in another forum,

"An excessive state tax payment cannot be deducted if, when the payment is made, the taxpayer did not have a reasonable expectation that the tax would actually be due. See Rev. Rul. 82-208, 1982-2 CB 58. "

Modulo any charitable carry forward from last year. =============== Good explanation.

In the Bay Area the penalty for being late on property tax payment is at least 10%. It's probably 10% plus interest.

Wow, that's a high late fee / penalty. For a 25% marginal taxpayer, the math can still favor the delayed payment. If a $1000 tax bill would be lost under the standard deduction, but returning $250, even a $100 penalty is still a positive result.

Note - My Schedule A is so high, I'm not in a position to try this process, and I know it's not for most people. One should be clear what the repercussions are for paying property tax late, and decide if it's worth the trouble.

Wow, that's a high late fee / penalty. ==========Standard late penalty for all of California. Interest is charged on both the tax and the penalty.

To do what was suggested here still isn't pushing more than 6 months into the future, which was the original question (cf. "prepay").