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What tax advice would you offer to Caitlin in planning for this situation?

Caitlin, a client of yours since you opened your practice, has become very intrigued by investing in the stock market. She has interest-bearing securities and dividend-paying stocks. She also owns U.S. Securities. She is considering selling $500,000 in stocks. She does not know if she should sell the additional stock for a loss to help offset the stock sale of $500,000. Caitlin called you to ask what tax consequences the interest and dividends will have along with the stock sale.

What tax advice would you offer to Caitlin in planning for this situation?

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