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Tax Research Issue Identification

Six years ago, Roberto acquired 500 shares of Roar Corporation stock directly from the
corporation for $500,000 in cash. This year, he sold 100 shares of the stock in Roar to Christopher for $40,000.
Required:
1. Identify at least three tax research issues regarding the stock sale you as Roberto’s tax advisor should consider? State each issue in the form of a question.
2. Do not attempt to answer the questions.
3. For at least one of the issues identified above, indicate the Internal Revenue Code Section that you would refer to in order to research the issue.

Instructions:

Your answers should be phrased in the form of a question.  Do not answer the questions.  A complete submission should include at least four questions in total.
Note that the questions you pose should be question that can only be answered by conducting tax research such as reviewing the tax code or case law.  It should not be a question of fact that can be answered by asking the client or reviewing the transaction documents.