Short description: The IRS normally doesn't let you deduct expenses incurred commuting to work. However, it grants an exception for expenses incurred bringing "tools of the trade" into work. Makes sense, right? But there's more: the deduction only covers the costs incurred for the tools, not any additional costs covered for you to commute with the tools.
How it plays out: A doctor who routinely commutes to her office via subway realizes she's going to have to take several patient charts home for the evening. If she takes a cab home, lugging the charts, she cannot deduct the expense. If she pays the cab to take her charts home for her (and keep the meter running until she arrives) and she takes the subway home, she can deduct the entire cab fare (which would be assuredly higher with the waiting time).
Perverse incentives created: Double-commuting, potential issues of leaving sensitive documents unattended.
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