I pay quarterly on self employment income but always owe on capital gains and some bit of unexpected income like a bonus. A rough estimate [our dates are different. and most frustrating we almost always get 'Amended' forms] suggest I'll owe $ 4K. I've alway's paid whatever balance was owed two business days before it's due. If I were charged a penalty I'd appeal.
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Tax Prep Anxiety
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I feel your pain. This was our first year we couldn't claim our daughter as a dependent, so we weren't sure what to expect; turns out we'll have a bill in the low four-digits, too. I do my taxes without any software beyond an Excel spreadsheet -- they're really simple -- but I have to say I'm tempted to use TurboTax this year, just to see if there's anything I'm missing.
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I'm already planning next year's taxes. I use the IRS W-4 withholding calculator. It is pretty accurate and I enter a worst case scenario of no charitable contributions. This give a very good indicator of what I will owe in 2015 for 2014. RIght now my bonuses are much bigger than I had planned for, so I will owe $30k more than I am withholding in 2014. Since I meet the safe harbor rule of withholding more than 110% of last years taxes paid, I will owe no penalty. So I'm putting $30k in a savings account and forgetting about it until next April. Life is good.
Tom
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