I didn't earn much money last year, so my 2008 W2 withholding will be enough to put me in safe harbor for 2008 without any estimated tax payments. However I am selling my business this year and will substantial capital gains, while 2009 will be pretty small. As such I won't benefit from the deduction on State income tax if I pay it next year with my tax return, so I want to pay estimated tax this year so I get the deduction in 2008.
The interesting thing, and the subject of my question, is that if I optimistically assume the stock market will go up 25% and pay state estimated tax accordingly, I maximize my 2008 deduction and reduce my 2008 Federal tax. If the market does not go up that much I will get a big state tax refund in 2009 and have to pay 2009 Federal tax on it, but thanks to the magic of AMT and very little income in 2009, the 2009 tax will be much less than the 2008 savings.
We all know the stock market probably isn't going up 25% this year, but it could.
Is there anything wrong with paying state estimated taxes optimistically, when I am not paying federal estimated taxes at all?