Facts Michael (a regional manager at D&M Co.) and Holly (a part-time HR representative) are married and live in New Jersey with their son Dwight. Michael has cancer and his physician, Dr. Halpert, recommends Holly attend a conference at a renowned clinic in Chicago, Illinois that teaches caregivers how to take better care of their loved ones with the illness. Holly takes the physician's advice and flies to Chicago for the conference, which is 5 days. Holly incurs the following expenses and uses some of her savings and inheritance to cover these costs: airfare [$1,200], meals [$75 per day], hotel [$325 per day], and fees to register for the conference [$2,300]. A prominent speaker at the conference, Toby, encouraged caregivers to travel with their patients to warmer climates where the change in scenery can improve their morale and overall well-being. Both Holly and Michael have always wanted to visit the Caribbean and dream of escaping to its beaches and pristine waters. Holly returns from the conference and immediately schedules a three-month trip to the Cayman Islands for Michael and herself to enjoy the warm weather and bask in the sunshine. A week into the trip (unbeknownst to Michael), his father, Oscar, and good friends Daryl, Meredith and Jo arrive and stay with the couple for a few weeks. Moreover, Holly is way over due for a new vehicle (her current car is 15 years old). She has heard many great things about plug-in electric vehicles and is considering purchasing one (e.g., a Tesla) rather than a standard car. She is wondering if there are tax benefits to purchasing an electric vehicle and if there is any difference for tax purposes between a brand new EV or a pre-owned EV. Holly and Michael's adjusted gross income (AGI) is $41,000. Although Michael and Holly have in-depth knowledge about paper and office supplies, they are unfamiliar with the tax implications of the above transactions and have asked for your help.

Required Holly and Michael file married filing jointly tax returns and have hired you to determine: (1) Whether the taxpayers can deduct as medical expenses any of the expenses for (a) Holly's conference in Chicago and (b) Michael and Holly's trip to the Cayman Islands? Include in your analysis the amount of the deduction, if any. (2) Whether there are tax benefits to purchasing a brand new or pre-owned plug-in electric vehicle? Make sure to analyze both sides of the argument(s) (e.g., analyze cases that are for and against your client's tax position). Note, if you include cases in your analysis, you should not only briefly summarize the relevant facts of the case, but also explain the court's reasoning behind its decision and apply your client's facts to the caselaw. type a Memorandum to the File.