To determine whether you should itemize your taxes or take the standard deduction when filing your tax return as an individual, the key factor is whether your total itemizable deductions exceed the standard deduction amount for your filing status.
Here's a breakdown relevant to the options you've given:
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The sum of your deductible contributions is less than $300: Not necessarily a trigger for itemizing. If your other deductions (such as mortgage interest, state and local taxes, etc.) do not add up to exceed the standard deduction, it is usually better to take the standard deduction.
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The sum of your deductible contributions exceeds $300: While this is a positive factor, it does not automatically mean you must itemize. You would still need to consider all other deductions to see if they exceed the standard deduction amount.
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You don't have any deductible contributions: If you have no deductible contributions or other itemizable expenses, you will likely not want to itemize.
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You donated to a religious institution: Donations to qualified charitable organizations (including religious institutions) can be itemized, but again, this alone does not require itemizing unless the total combined deductions exceed the standard deduction.
In conclusion, you must itemize your taxes only if the sum of your deductible contributions and any other itemizable deductions exceeds the standard deduction for your filing status. So, the most directly relevant option would be "The sum of your deductible contributions exceeds $300," but even that is not sufficient on its own; you'd consider all your deductions in the decision.