Federal Income Tax Archives

Can the IRS Collect Additional Taxes After Tax Restitution Is Paid?

In the case of Creel v. Commissioner, 419 F.3d 1135 (11th Cir. 2005), the IRS attempted to collect additional taxes, penalties, and interest from a taxpayer even after his criminal restitution obligation for the very same tax had been paid and satisfied. The district court had ordered the taxpayer to make restitution to the IRS…

Referrals/Leads Group is Not a Tax Exempt Entity

The tax laws in the United States provide for several types of tax-exempt organizations, including charities, social welfare organizations, and business leagues. In Private Letter Ruling 200709070 the IRS has brought attention to the requirements for organizations to qualify as a tax-exempt “business league.” The ruling denied tax-exempt status to a referral/leads group on the…

Video Poker Cannot Qualify as Professional Gambling

As technology and computers advance, there are more and more activities that put us, as humans, against computers. We, as humans, are in the position of having to game or strategize how to manipulate or beat computers to produce desired results. While it is not pointed out generally, whole industries are focused on doing just…

How HRAs Can Help Your Business

As a business owner, it’s always important to keep costs down while looking for opportunities to grow your business. One potential way to do this is through a Health Reimbursement Arrangement (HRA). An HRA is a tax-advantaged benefit that allows employers to reimburse employees for medical expenses on a tax-free basis. The employer contributes a…

Is Tournament Poker the Same as Live-Action Poker?

Are tournament poker losses subject to the same tax rules as live-action poker losses? This question turns on whether tournament poker is a “wagering activity.” Despite the amount of money at stake and the importance to taxpayers who gamble, the term wagering activity is not defined. This is where the recent Today, in Tschetschot v.…

The Hobby Loss Rules: Planning for Unprofitable Businesses

American culture still has a hint of the protestant work ethic. There are people in the United States who still work hard and are willing to take risks to make things happen. The country benefits if they are successful–particularly if it ends up in a viable commercial venture. Not all ventures end up being successful.…

Tax Basis Planning for Inherited Property

When you sell a property, you are typically required to pay income tax on the gain, which is calculated as the difference between the sales price and the tax basis. The tax basis is usually the amount that you paid to purchase or invest in the property plus the amount paid to improve the property.…

Retirement Accounts: Restorative Payments vs. Return of Human Capital

If you get something returned to you, you generally do not pay income tax on the return. You just get your property back. It can be difficult to tell whether you are getting your property back or getting some other property back. Is there a difference? Or should there be a difference? The court grappled…

IRS Clarifies Real Estate Broker 1099 Filing Requirements

The IRS relies on voluntary compliance from taxpayers, meaning that most people follow tax laws willingly. However, noncompliance can result in penalties, making it an incentive for individuals to comply. To help identify potentially taxable transactions, third parties are required to file information reporting forms with the IRS. For instance, real estate sales typically require…

When Tax-Free IRA Rollovers as Short-Term Loans Fail: Two Examples

Taxpayers often withdraw funds from their IRAs to cover short-term expenses with the hope that they can put the funds back in their IRA within the 60-day window for making a tax-free IRA rollover. This can work out well when taxpayers put the funds back into their IRAs within 60 days. When taxpayers miss the…