How the IRS feels like a thief taking our hard-earned money (my cartoon take on tax season frustrations)

But don't you think the system is deliberately complex to make people overpay? I've heard the tax prep industry literally lobbies to keep it complicated. Is there any way to simplify filing self-employment taxes without paying for expensive software?

The system is indeed more complex than it needs to be, and yes, tax preparation companies have lobbied against simplification efforts. However, I wouldn't say it's designed to make people overpay - rather, the complexity means many people miss legitimate deductions they're entitled to claim. For self-employment taxes without expensive software, the IRS Free File program partners with tax software companies to provide free filing options if your income is below certain thresholds. Alternatively, many local community organizations and libraries offer free tax preparation assistance. The key is keeping organized records throughout the year - tracking all business expenses, mileage, home office usage, and other potential deductions systematically.

Does it actually work with complex situations? I have W-2 income plus a side business plus some investment income, and my previous tax preparer charged me almost $700 to file last year.

How secure is this? I'm always nervous about uploading financial documents to websites I'm not familiar with. Do they store your documents after analyzing them?

It handled my fairly complex situation without issues. I have a full-time job plus two side businesses (one LLC and one sole proprietorship), plus rental income from a duplex. The system walked me through each income source separately and identified specific deductions for each category. It was much more thorough than the human preparer I used in previous years. Regarding security, they use bank-level encryption and don't store your actual documents after processing - only the extracted data which you can delete anytime. I was skeptical too, but their privacy policy is actually straightforward and they explain exactly how your data is handled. They're also very clear that they don't sell your information to third parties.

Wait, how does this actually work? Do they have some special connection to the IRS or something? I've been trying to reach someone about my amended return for 2 months.

Sounds like a scam to me. No way any service can get you through to the IRS faster than just calling directly. They're probably just recording your call and stealing your information.

They don't have a special IRS connection - they use a combination of automated dialing technology and call timing to navigate the IRS phone system efficiently. It's basically doing what you'd do manually (calling, navigating the prompts) but with technology that prevents disconnections and keeps your place in line. They explain it better in the video I linked. I understand the skepticism - I felt the same way. It's not about skipping the line but rather staying in the line without getting disconnected. They don't record your actual conversation with the IRS - they only connect the call and then drop off. The IRS call center confirms when an agent is ready to speak with you, and that's when Claimyr connects you directly.

As someone who dabbles in crypto, what's your advice for reporting small trades? I made maybe 50 trades last year but most were under $100. Do I really need to report every single one?

Technically, every crypto transaction is reportable, regardless of size. The IRS considers crypto property, not currency, so each trade is a taxable event. For those small trades under $100, you still need to report them, but there are tools that can help aggregate this information. For clients with numerous small trades, I recommend using crypto tax software like CoinTracker, Koinly, or TokenTax that can import your transaction history from exchanges and generate the necessary forms. These will calculate your gains/losses and produce a report you can use for your tax filing. Without such tools, reporting 50+ trades manually would be extremely time-consuming and error-prone.

For partial work from home situations, you can only deduct the business percentage of your internet if you're self-employed. W-2 employees lost the ability to deduct unreimbursed business expenses after the Tax Cuts and Jobs Act, unless you're certain specific professions like armed forces reservists, qualified performing artists, or fee-basis state/local government officials.