Golf does not qualify as a deductible expense just because you talk about business on the golf course. Golf does qualify for a deduction as associated entertainment when you have the right business discussion in a valid business setting before or after the golf, generally the same day.

This court case provides a great roadmap to the Section 105 medical reimbursement plan. The taxpayer hired her husband as a part-time employee. The husband had another job as a full-time employee where he elected a payroll deduction for a medical plan that covered himself and his family. In her proprietorship, the wife put a Section 105 medical plan in place that covered the employee-husband. He elected family coverage, and presto, the monies he paid to his full-time employer for medical coverage became a Section 105 medical reimbursement, deductible by the wife’s proprietorship.

When you start a new business activity or you do a business activity on the side, you must establish a profit motive. One easy way to demonstrate the profit motive is to show the time you spend on the activity. This taxpayer had no proof of time worked, so he looked suspicious to the court.

The corporate reimbursement to you, the employee, for the business use of your home office requires that you recognize the depreciation component of the reimbursement as if you had claimed the office in the home on your personal tax return.

The physician’s prescription often justifies a tax deduction, but not always. There are tax principles involved that need alignment for the deduction to prevail.

The one-person corporation is a separate legal entity from the owner. This means separate books for the corporation and expense reports from the owner-employee to prove business expenses. When you fail to document your golf or other expenses, two bad things happen.

The trade of a car on a lease is not a like-kind exchange. This is a sale of the old car and a lease of the new car. The sale part gives you a gain or a loss. In addition, the sale part generates a prepayment on the lease where you benefit with an amortization deduction.