Best tax prep tool for side hustlers

The tax software market is dominated by 3-4 giants (TurboTax, H&R Block, TaxAct), but the side hustle segment is fragmented with roughly 15-25 specialized or semi-specialized tools trying to capture this audience. The common failure is that most tools either oversimplify self-employment taxes or overcomplicate the UX by treating side hustlers like small business accountants. Pain points are brutal: unclear deduction categorization, poor mileage tracking integration, confusing quarterly payment calculations, and software that requires jumping between 3+ platforms. The real gap isn't in the filing itself—it's in the year-round tax planning and confidence building. Generic tax software assumes you file once a year; side hustlers need ongoing expense logging, real-time tax impact estimates, and clarity on what they actually owe before April 15th hits. A founder entering this space should focus obsessively on the deduction discovery layer (helping users identify what they can actually write off from multiple income streams) and real-time tax liability forecasting rather than just filing optimization. The market is growing because side gig participation has jumped 20-30% post-pandemic, but the tools haven't evolved to match the complexity.