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I'm planning to cut a check to the IRS for about $20,000 in April and couldn't be happier. Why you ask? Well that $20k has been sitting in a tax-exempt bond fund that returned about $800 in tax free interest. It also appreciated about $600, which was a bonus. Now I could have been much more conservative and put it in a money market fund and earned about $200. So the point is, $200 or $1400 - that's money in my pocket. I always withhold the bare minimum needed to avoid getting an under-withholding penalty.
Bonus tax advise: Check out Form 8880. If you make below certain income thresholds, are not claimed as a dependent, born before Jan 1 1995, and not a student, then you can receive a tax credit up to $1000 for contributions up to $2000 to an IRA. That's as much as a 50% match by the government! Go for the Roth. Thats all.
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