"when am I required
to file an itemized return vs standard deduction".
Simple answer to that one is the only time you could be REQUIRED to itemize instead of using your standard deduction is if you are filing married filing separately and your spouse is itemizing. When you file MFS both spouses have to file the same way--either both have to itemize or both have to use standard deduction.
The software will not "require" you to use itemized deductions at other times, and will default to standard deduction unless you enter enough itemized deductions to exceed your standard deduction, or unless you "force" itemized deductions.
HOW TO FORCE ITEMIZED DEDUCTIONS
https://ttlc.intuit.com/questions/1900142-how-do-i-change-from-the-standard-deduction-to-itemized-or...
**Disclaimer: Every effort has been made to offer the most correct information possible. The poster disclaims any legal responsibility for the accuracy of the information that is contained in this post.**
