I've been self-employed for about 5 years now, and I've tried almost all the tax software options. Here's my two cents: TurboTax Self-Employed is good but expensive. It does handle Schedule C well and provides good guidance, but you're paying a premium for the brand name. H&R Block Self-Employed is similar in quality and price to TurboTax. TaxAct and TaxSlayer both handle Schedule C for significantly less money. FreeTaxUSA is my personal favorite - it handles Schedule C perfectly well, the interface is clean, and it's WAY cheaper than TurboTax. If your situation is truly simple as you describe (just income, standard deduction, QBI, and SE tax), any of these will work fine. The difference mainly comes down to how much guidance you want and how much you're willing to pay for it.

One thing no one mentioned yet - if your self-employment income is below a certain threshold (I believe it's around $73,000 for 2024), you can use the IRS Free File program to file for free, including Schedule C. Different companies participate in this program, including some versions of TurboTax, TaxSlayer, etc. Just go through the IRS Free File portal rather than directly to the tax software websites, otherwise they'll try to upsell you. This is different from the "free" versions advertised on their websites, which typically don't support Schedule C filing.

I've dealt with this exact issue and wanted to share what worked for me. The IRS doesn't actually care about the $600 threshold itself - that's just when PayPal has to report to them. What matters is whether you actually made taxable income. Since these were your own funds moving between accounts, you have zero taxable income from these transactions. When you file, you'll want to include a brief explanation with your return stating that the 1099-K amounts represent personal transfers between your own accounts with no profit realized. Keep your PayPal transaction history and bank statements showing the money flow - this proves these weren't business transactions or income. I attached a simple one-page explanation to my return last year for a similar situation and never heard anything back from the IRS. The $47 in fees you paid actually works in your favor as documentation that this wasn't profitable activity. Don't stress too much about it - this is becoming a common issue and the IRS understands that not all 1099-K transactions represent taxable income.

The good news is you don't owe taxes on moving your own money around, even if PayPal reports it. Since these were transfers between your own accounts with no actual profit, you have zero taxable income from these transactions. When you file your taxes, include a brief explanation (just a paragraph) stating that the 1099-K amounts represent personal transfers between your own accounts with no income realized. Keep your PayPal transaction records and bank statements as backup documentation. The fact that you lost $47 in fees actually helps prove this wasn't a profitable business activity. This situation is becoming more common with the new $600 reporting threshold, so the IRS is getting familiar with these cases. As long as you can document that it was your own money moving in circles, you'll be fine. Don't overthink it - a simple, honest explanation attached to your return should prevent any issues. The IRS matching system flags discrepancies between 1099s and reported income, but providing upfront documentation explaining legitimate reasons for the difference is exactly what tax professionals recommend.

If you filed with a professional tax preparer last year, they might have your PIN or a copy of your return with the AGI on file. Worth giving them a call if that's how you filed. I completely forgot I had used H&R Block last year until I started panicking about my PIN, gave them a call, and they had everything I needed.

Another option if you're still stuck is to request an Identity Protection PIN (IP PIN) from the IRS if you qualify. This is different from your self-select PIN and can be used for identity verification when e-filing. You can check if you're eligible on the IRS website - they've expanded the program in recent years. Also, just a heads up that if you do end up creating a new self-select PIN this year, consider storing it in a password manager or writing it down somewhere safe along with your AGI. I learned this lesson the hard way after going through the same frustration you're experiencing! The IRS recommends keeping your prior year tax return easily accessible for exactly this reason.

As someone who's been freelancing in video editing for about 18 months now, I can share some real numbers. My effective tax rate ended up being around 18% of gross income after all deductions last year. Key deductions that made a big difference for me: - Home office (about 15% of my rent/utilities) - Equipment depreciation on my editing rig and monitors - Adobe Creative Suite and other software subscriptions - External storage and backup solutions - Partial car expenses for client meetings - Professional liability insurance The biggest surprise was how much the home office deduction helped - I have a dedicated editing room, so I can legitimately deduct that percentage of all housing costs including rent, utilities, even renter's insurance. I'd recommend setting aside 25% of each payment when starting out. Better to have a cushion than scramble to pay quarterly taxes. Once you get a feel for your actual effective rate after the first year, you can adjust accordingly. Also consider making estimated payments slightly higher than required - any overpayment becomes a refund, and it's better than owing penalties for underpayment.

One thing I wish I'd known before going freelance - don't forget about quarterly estimated tax payments! The IRS expects you to pay as you go, not just once a year. If you owe more than $1,000 when you file, you could face underpayment penalties even if you pay everything by the April deadline. The due dates are January 15, April 15, June 15, and September 15. I use Form 1040ES to calculate what I owe each quarter. Pro tip: if you had W-2 income the previous year, you can base your estimated payments on 100% of last year's tax liability (110% if your AGI was over $150k) and avoid penalties even if you end up owing more. For video editors specifically, income can be pretty irregular - some months feast, some months famine. I found it helpful to set aside 25-30% of every payment into a separate tax savings account, then make estimated payments from there. Takes the stress out of those quarterly deadlines when you know the money is already saved up.

Has anyone considered the timing here? Since the wife started the FSA in July, couldn't they argue that the HSA was fine for January-June, and then became ineligible only from July onward? That way they'd only need to withdraw half the year's HSA contributions instead of all of it.

Just be really careful about the timing of any HSA withdrawals if you go that route! I learned the hard way that excess contributions need to be withdrawn by the tax filing deadline (including extensions) to avoid the 6% excise tax penalty that applies each year the excess remains in the account. Also, since you mentioned you've already contributed $8,300 for the full year, make sure your payroll department stops any ongoing HSA contributions immediately while you sort this out. You don't want to keep adding to the problem while you're trying to fix it. One more thing - document everything! Keep records of when your wife's FSA started, any communications with HR about potential changes, and if you do need to make HSA withdrawals, keep all the paperwork from your HSA provider. You'll need this documentation for your tax return.