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The last time we itemized was 2014. Medical expenses >7.5% of AGI was our big driver to allow itemization that year and earlier years. Had a positive job change in 2014, so in 2015, income was high enough most medical was not deductible. Tried itemizing in 2015, and just couldn't make it.

Its somewhat ironic to me that itemization benefited me at a lower middle class salary, but not at an upper middle class salary.
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