Having been through an audit, I’m convinced that there is no real way to accommodate the tax system while being fair to yourself. Essentially, if you file your taxes every year (assuming US) claiming that information that has been tattled to the IRS for another party’s benefit, eg. 1099 misc, 1099 B etc, you really can just wait for the audit that likely will never come, let them do all the work, pay the bill, and say oooops, golly gee, I’m just an idiot who didn’t know better. Unless you’re making millions you are very unlikely to make it on the radar. As an option, make a business out of some hobby you spend a lot of money on. File a schedule C, show a loss for 3-5 years fold the company rinse and repeat. It’s a shame, but W2 people pay the vast majority of income tax, while there are thousands of loopholes for the wealthy and businesses. No real surprise there I guess, those who have the gold make the rules.