I'm interested in shifting state taxes as part of a deduction-bunching strategy. The year 2010 will be an itemized-deduction year for me, and 2011 a standard deduction year. For this reason I'd like to pay as little state tax in 2011 as possible (minimize withholding and estimated taxes). But, since I'll have some state-taxable income in 2011, I'll have a state tax liability. I see two ways around this.
One is to simply have a big state tax bill, payable in 2012 when I file my 2011 return. Yes, I'll pay 5% or so interest, but meanwhile I saved 25% (or whatever my fed marginal rate is) on the state tax payment I shifted from the standard-deduction year 2011 to the next itemized-deduction year 2012. Or maybe the penalty will be much larger, since I so obviously underpaid in 2011 ?
Another is to grossly over-withhold state taxes in 2010, so I have a big state tax refund on my 2010 return, but to check the box to put that refund towards my 2011 taxes. Then I won't need to withhold anything in 2011 to avoid a penalty (I will have "prepaid" my 2011 state taxes). But, I have a sneaky feeling that the state will still send me a 1099- G for that refund, even though I put it towards next year's taxes, so this scheme won't work either.
Thoughts ? Thanks.