If you build a mini business empire and it subsequently fails, a small consolation prize might be a net operating loss carryover that will shelter some or all of your more modest income for many years. Of course NOLs are only one among many carryovers that need tracking. In my experience the tracking often leaves much to be desired. Changes in tax preparers or even software can result in the loss of valuable carryovers. But that is not the worst of it...
Intentionally Filing a Defective Tax Return
Creativity on a tax return is a natural tendency. Many strategies and behaviors we know are wrong, e.g. not reporting all income. However, is it ever okay to disregard some deductions and pay more tax? At first glance, it would seem that the IRS should like the idea of more reported income and a higher tax liability attached to the additional income. The IRS does not.