Problem
Ron sold his sailboat for a $5,000 loss in the current year due to medical issues. His spouse wants him to sell his Harley Davidson motorcycle because her brother broke his leg while riding his motorcycle. Since Ron no longer has anyone to ride with him, he is seriously accepting his wife's advice. Because the motorcycle is a classic, Ron has received two offers. Each offer would result in a $5,000 gain. Joe would like to purchase the motorcycle before Christmas, and Jeff would like to purchase it after New Year's Day.
Explain one relevant tax issue for Ron and describe the tax advantages and disadvantages of what he may be faced with.