In December, T.D. Weber evaluated his stock portfolio and found that his DLW Inc. common stock had declined in value since he purchased it. He decides to sell the DLW stock on December 15. However, he would like to retain an interest in the company. So, knowing that he needs to avoid the wash sale rules, when he sells the common stock on December 15th, T.D. simultaneously purchases an equivalent amount of preferred stock in DLW Inc. On January 17 of the next year, he sells the preferred stock and repurchases DLW common stock.

Your post should include with details:

• What do you think of his strategy?
• How are the wash sale rules involved with this situation?

Link: https://www.irs.gov/publications/p550#en_US_2019_publink100010741