In which situation is itemizing deductions advantageous?

Itemizing deductions is advantageous primarily when the total amount of itemized deductions surpasses the standard deduction available for a taxpayer's filing status. This occurs because taxpayers are allowed to choose the greater of the two amounts—itemized deductions or the standard deduction—when calculating their taxable income.

For instance, if an individual has significant deductible expenses related to mortgage interest, medical expenses, or charitable contributions that cumulatively exceed the standard deduction, it would be more beneficial to itemize these deductions. This can lead to a lower taxable income and ultimately result in a smaller tax liability.

The other situations mentioned may have their benefits but do not inherently lead to itemizing being advantageous. For example, having no dependents or filing jointly doesn't directly affect the benefits of itemizing versus taking the standard deduction. Additionally, a lower income doesn't directly imply that itemizing will be beneficial unless it is accompanied by substantial deductible expenses.