Tax Planning – Stock Investment Strategies – II

In the last couple of posts, we been looking at how Tax planning can have an effect in your tax preparation. We saw the difference between Tax Planning and Tax preparation. We also started digging in deep on how the cost basis and stock selling strategy can save you some money. In the previous post, I started explaining about different types of determining cost basis and will complete in this post. At the end of this post, you will know which methods helps on different situations. So read on.

Check out the cost basis using FIFO method before moving on to read so you can better understand the difference.

Average cost is another method for determining cost basis and is only used with investment/mutual funds. To determine the average cost, the total cost of all shares purchased including any invested dividends is divided by the total number of shares held.


Once this method is used, it must be used each time the taxpayer sells shares in a mutual funds. This method is most effective if the shares purchased first have the lowest cost basis.


Average cost has 2 different ways of calculating according to the stock purchased periods. The single category method is when the investor takes all of the purchase amounts and divides by total number of shares owned. The double category method sorts the total shares owned into a short-term and a long-term holding period. Then, the average cost for each category is identified.


For example, Jan buys the Vanguard growth fund

  • 200 shares on January 3, 2001 at $20/share

  • 300 shares on September 5, 2002 at $25/share

  • 200 shares on April 20, 2008 at $22/share

On Oct 15, 2009 she sold 500 shares at $20/share. What is her cost basis according to the average cost method?


According to the single category average cost method, she would take an average of the purchase prices and divide by the total number of shares owned:

  • 200 shares at $20 = $4,000

  • 300 shares at $25 = $7,500

  • 200 shares at $22 = $4,400

  • Total cost = $15,900

  • Total shares = 700

  • Average cost per share = $22.71

So the gain/loss for this sale was:

  • 500 shares ($20 – $22.71) = -$1135.50

Therefore, Jan had a net loss of = -$1135.50


The specific share identification method implies that specific shares are used to apply against the shares sold.


Before selling shares, the shareholder must inform the broker or fund company regarding which shares are to be sold. These instructions must be given at the time of sale or transfer, not later. The broker or agent must confirm this request within a reasonable time after the sale.


This method can be used effectively only if the shareholder has kept accurate records and has followed through on the receipt of confirmations from the broker. It allows the shareholder to control the capital gains taxes that he or she has to pay because this can be determined by selecting the shares to sell. You can tell your broker to sell your highest-cost shares when unloading part of your holdings in a stock. Using this “specific ID method” requires you to identify the shares to be sold by specifying their cost and purchase dates. You must also receive a written confirmation of your instructions from the broker or keep a record of your oral instructions. Put this in your tax file for safekeeping.


Which method is suitable and when?

Specific ID method is the best method for tax purposes because the investor has absolute control over how much the gain from a sale would be. Long term or short term gains can also be controlled. This is the preferred tax basis method for investors who actively manage their portfolio for tax efficiency. It is also not the most cost effective because of all of the effort that is required for proper record-keeping.


If you don’t follow th procedure, you must use the first-in, first-out (FIFO) method, meaning the shares you bought first are considered sold first. Those were likely the cheapest — giving you the biggest possible tax hit. The point to remember is that you must take action at the time of sale to use the specific ID method.

Short term Vs Long Term

If you have both unrealized gains and losses in your portfolio, but want to make some sales in a certain way matching them property to get the best effect. 
First, the general rule is try to sell long-term holdings (held over 12 months) first to benefit from the 15% maximum long-term capital gains rate. Then, unload your short-term holdings.


Then in order to offer offset those gains, you can sell the loser stocks for loss to balance it out. You will generally get the most tax-saving for the buck by selling short-term holdings for a short- term loss by taking advantage of short-term losses offsetting short-term gains which would otherwise be taxed at the regular income tax rate and any leftovers then offset long-term (15%) gains.

By following the above strategies matching your situation, you can either save some money by not paying to uncle sam way beyond the tax season. That concludes the tax planning – Stock investment strategy by doing cost basis analysis.

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