Deduct up to 50% of entertainment costs, or gift costs up to $25 each, as long as they are ordinary and necessary for your rental investment. Any item that might be considered either a gift or entertainment generally will be considered entertainment. However, if you give an item that is intended to be used at a later date, treat it as a gift.
If you give someone tickets to a theater performance or sporting event and you do not go, you have a choice of treating the cost as either a gift expense or an entertainment expense, whichever is to your advantage. For example, if the tickets cost $20 you would treat it as a gift so you could deduct the whole amount, but if the tickets were $100 dollars then you would want to treat it as an entertainment expense so you can write-off $50 instead of $25.
If you go with the person to the event, you must treat the cost of the tickets as an entertainment expense and cannot treat it as a gift expense.
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