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Should you take long-term capital gains in 2010?

For many taxpayers, 2010 might be their last chance to pay a “bargain” 15% federal tax rate for long-term capital gains. Individuals who have appreciated assets should consider selling them this year and paying the tax for 2010. Since 2010 is more than half over, it’s time to think about year-end tax planning. Some transactions take months to execute, so the time to start taking action may be now.

The Bush tax cuts enacted in 2001 are expiring after 2010. If Congress does nothing, the maximum federal long-term capital gains rate will increase from 15% to 20%. That’s a 33 1/3% increase! Some low income taxpayers are actually currently eligible for a 0% rate for long-term capital gains.

When planning to take long-term capital gains during 2010, be aware that the “wash sale” rules disallowing losses when the same or similar property is sold and repurchased during the period 30 days before and 30 days after selling an asset does not apply to gains. In essence, you can elect to report gains for your property by structuring a sale followed by a repurchase. There is still a possibility the IRS could challenge such a transaction on a substance versus form argument, especially for transactions with related parties.

When evaluating whether to sell and repurchase property, consider whether selling expenses could exceed the tax benefit from the transaction.

President Obama has proposed extending the Bush tax cuts for married persons filing joint income tax returns who have adjusted gross income of less than $250,000 and for single persons with adjusted gross income of less than $200,000. We probably won’t know if Congress will enact this proposal until late 2011. We have seen that Congress is finding it difficult to pass much tax legislation this year, including extension of the estate tax and many tax extenders. It may be wise to take defensive action.

A 3.8% Medicare tax on investment income of high-income taxpayers, including long-term capital gains, has already been enacted effective in 2013.

When the stock market and real estate markets are weak, it seems strange to talk about tax planning for long-term capital gains. The value changes for items are uneven. Some taxpayers could still be holding substantially appreciated property, like Google stock that they bought shortly after the company went public, or a rental home they bought thirty years ago.

Always consult with a tax advisor before making a major tax planning decision.

IRS Circular 230 Disclosure: As required by U.S. Treasury Regulations, you are hereby advised that any written tax advice contained in this communication was not written or intended to be used (and cannot be used) by any taxpayer for the purpose of avoiding penalties that may be imposed under the U.S. Internal Revenue Code.

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4 Responses to “Should you take long-term capital gains in 2010?”

  • Bruce Brumberg Says:

    Good reminder about the wash sale risks of selling to take advantage of lower rates and then repurchasing again in early 2011. Do you have any examples of the IRS recharacterizing transaction related to stock holdings?

    Is the analysis for the tax increase really 33 1/3% or just 5%. A 5% increase in the stock price would just about cover additional taxes owned by selling the stock or other assets at the 20% rate instead of 15%.

    For a series of articles that look at the impact of the tax increase on various strategies for company stock and option holdings, see the Financial Planning: Advanced Strategies section on http://www.myStockOptions.com (at http://bit.ly/c2jIN4)

    Do you think there will be any tax legislation this year on capital gains or dividends and thus we would go back to the pre Bush Tax Cut days? The Obama proposal is almost like a “tax cut” compared to them.

  • admin Says:

    As I said in the post, the wash sale rules actually apply to loss sales. 5% / 15% = 33 1/3%. However you cut it, the increase is significant. You’re right that a 5% increase in the selling price would just about “make it up”, but if you sold and bought another similar stock, you would probably have about the same gain, and pay less income tax.

    Based on what has been happening in Congress so far this year, I don’t expect to see a major tax law change until at least late 2011, which is making it really hard to plan. If Congress does nothing, we literally will be in the pre Bush tax cut days.

  • Catherine Says:

    If you sell investment property in California, what is the percentage of taxes you will pay for 2010 and 2011? How much is the State of California going to charge you for investment property capital gains?

  • admin Says:

    California gives no break for capital gains. Net capital gains are taxed like ordinary income.

    California has a graduated rate schedule. The maximum rate of 9.3% applies for married filing a joint return with taxable income exceeding $93.532 or single persons with taxable income exceeding $46,766.

    A 1% surtax applies for income exceeding $1 million.

    Governor Brown is seeking a tax increase, so the rates might change for 2011.

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