Let me tell you about Marcus. He’s a full-time Uber driver operating out of downtown Chicago. Last year, he received a CP2000 notice from the IRS. They weren't just asking friendly questions; they were proposing a $4,200 adjustment in back taxes , plus potential penalties. Why? Because Marcus claimed 55,000 business miles on his Schedule C, significantly offsetting his entire $42,000 gross income. On paper, his business operated at a substantial loss. The IRS automated systems flagged this discrepancy. They asked for his mileage log. Marcus sent them a spiral notebook with a few scribbled dates and some guesstimated weekly totals. The auditor disallowed the undocumented miles. Without a contemporaneous, compliant log, he lost his biggest deduction. He faced a significant unexpected tax liability and financial stress. You cannot simply estimate your way through gig economy taxes . The IRS has fully automated their document matching systems, utilizing advanced dat...