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Imagine today was 12/29/2019 and Amelia, a cash method taxpayer, come to you with a few questions regarding her tax planning for the 2020. Below

Imagine today was 12/29/2019 and Amelia, a cash method taxpayer, come to you with a few questions regarding her tax planning for the 2020. Below are a few things that Amelia was considering and would like to consult with you:

  1. Amelia was considering getting married in 2020 to her boyfriend, who is currently unemployed and now living in his moms basement training 24/7 to become a professional Mario Kart player. However, she afraid that after getting married, her tax would be doubled because now she also has to pay her husbands tax. She is quite confused about this part and want to check how much would her tax go up if she gets married this year.
  2. Amelia received a $5000 worth of Apple stock in 09/01/2019 from her father as a birthday gift. She was considering selling all of those sometime in September 2020 because Apple normally hold an annual event at that time and stocks tend to go up around that period. However, Amelia worry that if she sells stocks at that time, she will have to pay a much higher tax. Amelia was considering selling those stocks tomorrow (12/30/2019) because her income this year is still pretty low ($30k). Amelia would have the same job for 2020 so her expected income again would be $30k.

What are your thoughts and advice for Amelia? Provide detailed explanation for each concerns.

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