TurboTax wins for the most layered personal returns — investments, property, side income — with its Intuit Assist tool citing specific IRS codes when you ask whether a particular expense is deductible, at the highest price point of the three. H&R Block wins on value for self-employed and freelance filers specifically, generally coming in cheaper than TurboTax at a comparable tier while still offering an AI assistant with a live human tax professional to escalate to. FlyFin wins for freelancers who want the deduction-finding done for them: its AI scans your actual expenses across 200+ categories and pairs that with a real CPA who files the return. All three now blend AI with human backup rather than replacing a tax professional outright — the real choice is which one's specific tax situation and price point actually fits yours.
Where each one actually wins
TurboTax remains the most widely used consumer tax platform in the US, and its Intuit Assist feature specifically cites the IRS code behind a deduction or credit answer rather than giving a vague yes-or-no. It's the strongest fit for a more complex personal return — multiple income sources, investments, rental property — where that specificity actually matters, at $39-159 for federal filing depending on complexity.
H&R Block generally undercuts TurboTax on price for self-employed and gig-work filers specifically, while its AI Tax Assist answers real-time questions about deductions and credits with a documented escalation path to a live tax professional when the AI can't answer confidently. For a freelancer or side-gig filer choosing on price without wanting to give up human backup entirely, this is the stronger value.
FlyFin is built specifically around freelancers and the self-employed: its AI Deduction Finder scans your actual expenses across more than 200 write-off categories automatically, then a certified CPA reviews and files the return rather than leaving you to self-file based on the AI's suggestions alone. It's billed annually rather than as a simple monthly fee.
Quick comparison
| Tool | Core strength | Starting price | Best fit |
|---|---|---|---|
| TurboTax | Layered personal returns, cites IRS codes | $39-159 federal | Investments, property, multiple income sources |
| H&R Block | Best price for self-employed/freelance | $65 (Deluxe) | Gig work and freelance income on a budget |
| FlyFin | AI deduction finder + real CPA filing | ~$16/mo (billed annually) | Freelancers who want deductions found for them |
Which one should you actually use?
Start with H&R Block if you're self-employed or freelance and want the best price without giving up a human backup option. Move to TurboTax if your return is genuinely complex — investments, property, multiple income streams — and you want an AI assistant that cites the specific tax code behind its answers. Use FlyFin if finding every legitimate deduction automatically, then having a CPA actually file it, matters more than doing any of the work yourself.
FAQ
Can I trust an AI tax assistant's answer without a human checking it? Not entirely — all three pair their AI with human backup for a reason, and a wrong deduction claim has real financial and legal consequences. Use the AI to find and understand options quickly, but verify anything unusual or high-stakes with the human professional layer each service provides.
Is it worth paying more for TurboTax if H&R Block is cheaper for self-employed filers? Only if your return has the specific complexity TurboTax is stronger at — investments, rental property, or multiple income sources with different tax treatment. A straightforward freelance return without those complications is usually served just as well by H&R Block's more affordable option.
How does FlyFin's AI deduction finder actually work? It connects to your bank and expense accounts and scans transactions against IRS deduction categories automatically, flagging potential write-offs across your actual spending rather than requiring you to remember and categorize every expense yourself.
Do any of these tools file state taxes too, or just federal? All three support state filing, typically as an add-on cost separate from the federal filing fee — factor that into your total cost comparison, since state fees vary meaningfully between providers and can change the cheaper option once you add both.
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*Ratings and pricing reviewed monthly. Last updated September 2026.*
Bogdex · Founder & editor, woska
Bogdex builds and curates woska, testing AI tools against real workflows to judge which ones actually save time rather than which have the longest feature list.