If you're a freelancer or 1099 contractor in the US, the IRS expects you to pay estimated taxes four times a year — and figuring out exactly how much you owe each quarter is one of the most stressful parts of self-employment. Guess too low, and you risk an underpayment penalty. Guess too high, and you're lending the government your cash flow interest-free. The good news: a new generation of AI-powered tools now scans your bank transactions, flags deductions automatically, and calculates your quarterly estimate in real time — no spreadsheet required. Here's how the top options compare. Quick Comparison Tool Best For Starting Price AI Deduction Finding CPA Filing Support Keeper Tax Gig workers wanting a simple, chat-style interface Low monthly fee (bundled) Yes Yes Hurdlr Budget-conscious freelancers who want mileage + estimates Free tier available Yes No FlyFin Freelancers with messy 1099 income who want CPA backup ~$16–29/month (billed annually) Yes Yes QuickBooks Self-E...