TBF, deductions aren't "gaming the system", but rather a very limited form of what companies get to do for all of their expenses. I agree they're a pain in the ass and much nicer to not do personally, but I don't see much of an alternative (besides not itemizing). But really if you want to make the tax code more fair, the restrictions on individual deductions for transportation, housing, food, etc should be eliminated. Those expenses are in fact required for you to earn your income.