Best Tax Software for 2026 (And Handling Market Drops) SB1805

What It Covers

Robert Farrington from The College Investor breaks down the best tax software options for 2025 returns, covering eight distinct filer categories from basic W-2 workers to crypto traders and landlords. The episode also examines the recent precious metals and crypto market collapse, including a suspicious $200 million leveraged short position placed hours before silver dropped 30%.

Key Questions Answered

• •Best Overall Tax Software: FreeTaxUSA earns the top overall pick for 2025 tax filing. Federal filing is completely free, and state returns cost $15.99 each — lower than nearly every competitor. It handles the most common filing situations, including W-2 income and standard 1099 forms, with straightforward data entry. Residents of the nine states with no income tax pay nothing at all. Professional audit support is available as an add-on for $44.99.
• •Truly Free Filing Option: Cash App Taxes is the top pick for filers who qualify for completely free federal and state returns. The key limitation is single-state filing only — anyone filing in two states, such as New York and New Jersey residents who cross state lines for work, cannot use it. It also excludes K-1 income and certain tax credits. Simple W-2 filers with student loan interest and no side income are the ideal users.
• •Best for Investors and Crypto Traders: TurboTax leads for heavy investors and crypto traders specifically because of its brokerage and exchange integrations. It connects directly with Coinbase and major brokerages, auto-importing transaction data to populate Form 8949. This matters most in 2025 because the new 1099-DA digital asset form means the IRS now cross-references centralized exchange trades. Filers who moved crypto off-exchange must manually reconcile transfers or risk overstating taxable proceeds.
• •Best Value for Landlords and Side Hustlers: TaxSlayer's Classic tier at $22.99 includes all forms needed for Schedule E rental income, depreciation schedules, and Schedule C self-employment income — forms that trigger premium tier upgrades at TurboTax and H&R Block, pushing costs above $100. Upsells at TaxSlayer are limited to professional support access only, not additional form access. Side hustlers with basic income can also start with free Cash App Taxes before graduating to TaxSlayer.
• •Tax Filing vs. Tax Planning: Filing a tax return is data entry — a report card on the prior year — and software handles that adequately. Actual tax savings come from year-round planning with a CPA or accountant who identifies which expenses to track, which accounts to fund, and which deductions apply before the tax year closes. Meeting monthly with a tax professional, rather than annually at filing time, produces the most consistent reduction in taxable income.
• •Concentrated Asset Volatility: Silver dropped over 25% and gold posted its largest single-day decline since the early 1980s during the recent selloff. The core lesson is that narrowing investment focus to a single asset class — whether silver, Bitcoin, or an individual stock — dramatically widens the range of possible returns in both directions. Assets without underlying earnings or economic output are inherently more volatile than diversified equity portfolios tied to business cash flows.