Yeah… My wife and I together make six figures a year (if only just barely), own a home with a mortgage, and have a kid, and I’ve *never *had the itemized deduction exceed the standardized deduction. I think you’ve either got to specifically structure your financial life around taking deductions, or make “'It’s one banana, what could it cost” money to have itemized deductions make any sense, at which point, why are you complaining about the cost of tax prep anyway? A tax accountant doesn’t cost that much.