Tax Software Buying Guide: Match to Your Situation
By Itai Varochik | Updated February 18, 2026 | 3 min read
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Do you even need paid tax software?
If you have a simple W-2 job, take the standard deduction, and don't have investment income — you probably don't need to pay anything. Cash App Taxes (free) or FreeTaxUSA ($0-$15) handle simple returns with the same accuracy guarantees as TurboTax.
Simple w-2 + standard deduction
Best choice: Cash App Taxes (free) or FreeTaxUSA ($0 federal, $14.99 state). Don't pay $70+ for TurboTax when free alternatives handle simple returns with the same accuracy.
Homeowner with itemized deductions
Best choice: H&R Block Deluxe ($55) or TurboTax Deluxe ($69). Both guide you through mortgage interest, property taxes, and charitable donations efficiently.
Crypto and investment traders
Best choice: TurboTax Premier ($89) + CoinTracker/Koinly for crypto. TurboTax Premier handles stock/ETF imports automatically. For crypto, use CoinTracker ($59-$199) or Koinly ($49-$279) to generate your tax forms.
Self-employed / freelancers
Best choice: TurboTax Self-Employed ($129) or H&R Block Premium ($85). Self-employment requires tracking business income, expenses, home office deductions, and estimated tax payments.
Frequently Asked Questions
Is TurboTax Free really free?
Only for very simple returns (single W-2, standard deduction). Most filers get upsold. For truly free filing, try Cash App Taxes or IRS Free File.
TurboTax vs H&R Block - which is cheaper?
H&R Block is 20-30% cheaper across all tiers: Deluxe $55 vs $69, Premium $85 vs $99, state $45 vs $59.