Year-End Tax Management Strategies

by Terry D. Sandven, Portfolio Strategy Group
U.S. Bancorp Piper Jaffray

Portfolio management is a dynamic process of monitoring and adjusting investment portfolios. Included in this process is the effective and efficient management of taxes. To that end, while we encourage investors to consult with their tax advisors to address specific needs, we offer several strategies that may assist investors to reduce their tax liabilities as well as to determine if opportunities exist.
30-Day Wash SalesWash sales are defined as the purchase and sale of a security either simultaneously or within a short period of time. Wash sales apply to individuals who want to take a tax loss in the current year on shares of a company that have declined in value from the purchase price. Under IRS rules, a loss on the sale of a stock may not be used for tax loss purposes if the same stock, or an equivalent one, is purchased within 30 days before or after the date of sale. As such, investors who want to own shares of a particular company at year-end have until November 30 to capitalize on wash sales. To adhere to the IRS 30-day wash rule, these investors have two options:
Option 1: Purchasing additional shares on or before November 30 allows enough time to sell the initial position by December 31. Risks of this option center primarily on exposure. The strategy increases exposure to a particular company twofold during the 30-day waiting period.
Option 2: Investors may sell the initial position at any time during 1999 to realize the loss in 1999. (However, if investors wish to reinstate the position before the last day of the current year, the sale must be made on or before November 30.) Risks of this option center primarily on lack of exposure. This option eliminates exposure to a particular company during the 30-day waiting period. As such, the opportunity costs, should the stock appreciate, could diminish tax benefits.
Upgrade Equity PortfoliosA popular year-end tax management strategy is to upgrade the equity portfolio. The concept involves swapping out of "losers" and into peers or companies where earnings are generally regarded as being more visible, while realizing a tax loss in the process. Earnings visibility is widely regarded as being important as we approach Y2K and the new millennium.
Bond SwapsA bond swap, for tax purposes, involves selling bonds that are owned at higher prices with the sale proceeds used to purchase other bonds, presumably those with similar characteristics. The realized loss is often used to offset other capital gains, thus reducing the overall tax liability.

Investors have until the end of the calendar year to execute tax swaps. We are also mindful that the pressures of demand over available supply typically increase towards late December. Thus, we encourage investors to assess their tax swap opportunities before year-end.
The advantages of bond swaps extend beyond tax benefits; swaps may also be used to enhance income streams, improve credit quality, extend maturities, or improve call protection.
Retirement PlansInvestors can reduce their taxable income by putting maximum allowable pretax dollars into 401(k) or 403(b) plans as well as IRAs. To be sure, this strategy applies throughout the entire year and not just year-end.
GiftingInvestment gifts meet several objectives, including estate size reduction. Individuals are allowed to give up to $10,000 per year to any person without incurring taxes on the gift.
Charitable ContributionsInvestors may benefit more from donating appreciated assets versus giving cash. In most cases, investors avoid paying capital gains on donated appreciated assets. Hence, not only are taxes avoided on capital gains, the charitable institution receives a larger gift compared to cash paid from after-tax dollars.

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