I went through this exact same situation last year with about $25 in stock profits. After reading through all the comments here, I decided to call the IRS directly (yes, it took forever to get through). The agent told me something that might help clarify things for everyone: The key isn't the profit amount - it's whether your broker reported the cost basis to the IRS on your 1099-B. Look at your 1099-B form and check if there's basis information included. If it shows "basis reported to IRS" or has the cost basis filled in, then the IRS already has all the information they need and you likely don't need Form 8453. However, if your 1099-B shows the sale proceeds but NOT the cost basis (common with older accounts or certain types of trades), then yes, you need to send Form 8453 with documentation regardless of the tiny profit amount. For my $25 situation, it turned out my broker HAD reported the basis, so I didn't need to send anything extra. Check your 1099-B first before assuming you need to mail anything!

This is really helpful information from everyone! I'm dealing with a similar situation but with crypto trades instead of stocks. Made about $45 in profits from some Bitcoin trades last year and my tax software is also telling me I need Form 8453. From what I'm reading here, it sounds like the key is whether the exchanges reported my cost basis to the IRS. Most crypto exchanges don't provide 1099-B forms like stock brokers do - they usually just give you a 1099-K or their own transaction summary. Does anyone know if the same "basis reported to IRS" rule applies to cryptocurrency transactions, or do crypto trades automatically require the Form 8453 documentation regardless of the amount? I'm trying to figure out if I can avoid mailing in 20+ pages of crypto transaction records for such a small gain.

Whatever you do, stay away from the "free" tax preparation software. I tried using FreeTaxUSA for my side gigs last year and it was TERRIBLE for handling multiple 1099s properly. Ended up having to pay a professional to fix all the mistakes after I got an audit notice.

Reading through all these comments, I'm seeing a lot of different options mentioned. As someone who's dealt with IRS compliance issues for small businesses, I'd suggest being really careful about who you trust with a complex situation like yours. The $800 Jackson Hewitt quote isn't unreasonable given your circumstances - 18 income sources plus an unfiled year is genuinely complex work. But before you commit, I'd recommend getting a second opinion from an Enrolled Agent (EA) or CPA who specializes in gig worker taxes. They're often more experienced with the specific deductions and strategies that can really benefit someone in your situation. Also, since you mentioned getting over $6,300 back, make sure whoever prepares your return explains the refund breakdown. With that much self-employment income, you want to understand if you should be making quarterly estimated payments going forward to avoid penalties next year. That's something a good tax professional should definitely discuss with you as part of their service.

I fixed this exact problem last year by using the "Married but withhold at higher Single rate" checkbox on my W-4. It's simpler than trying to calculate an exact additional withholding amount. This basically makes your withholding closer to what a single person would pay on the same income, which is usually about right when both spouses work. We had the EXACT same situation - my wife's taxes were like 11% and mine were only 6%. After checking that box and submitting a new W-4, my withholding went up to about 15%, which was a little high, but we'd rather get a refund than owe.

This is such a frustrating but common issue! I went through the exact same thing last year. The key problem is that the W-4 form changed significantly in 2020, and most people (including HR departments) don't fully understand how it works for two-earner households. What's happening is that each employer is calculating withholding as if that's your only household income. So your husband's employer sees his $78K salary and thinks "married filing jointly with one child = low tax burden" without knowing about your $115K income that pushes your combined household into much higher tax brackets. Here's what worked for me: I used the IRS Withholding Estimator (irs.gov/W4App) with both our incomes and it calculated that we needed an additional $520 per month withheld from my husband's paycheck. We put this amount in Step 4(c) of his W-4 as "Extra withholding per pay period." For your 2024 taxes that you'll owe, definitely file by April 15th even if you can't pay the full amount immediately. The failure-to-file penalty is much worse than failure-to-pay. You can set up a payment plan online at irs.gov if needed. The silver lining is that once you fix the W-4 forms properly, this won't happen again in 2025!

In the vast majority of cases, taking the SEHID is absolutely beneficial and you should definitely claim it. With $14,000 in premiums, that's a substantial deduction that will save you money on both income tax and self-employment tax. The scenarios where it might not be advantageous are extremely rare - things like if you're right at the edge of qualifying for income-based student loan forgiveness programs that require higher AGI, or if you're applying for mortgages where they want to see higher income. But for pure tax purposes, it's almost always a win. One thing to double-check though - make sure you meet all the eligibility requirements. You need to have net self-employment income, and if you're married and your spouse has access to employer health insurance that covers you, that could disqualify you from taking the deduction. The fact that your accountant mentioned it suggests they think you're eligible and it would benefit you. I'd trust their judgment - they can see your full tax picture and calculate the exact impact for your situation.

One additional point to consider that I haven't seen mentioned yet - the timing of when you take the SEHID can matter if you're making estimated quarterly tax payments throughout the year. Since the deduction reduces both your income tax and self-employment tax liability, it can affect how much you should be paying in estimated taxes. If you're planning to take the SEHID, make sure you factor that into your quarterly payment calculations so you don't overpay during the year. I learned this the hard way my first year of self-employment - I was calculating my estimated payments based on my full income without accounting for the SEHID, and ended up giving the government an interest-free loan for months. Also, keep good records of all your health insurance premium payments throughout the year. The IRS may want documentation if they ever audit, so having receipts or bank statements showing the payments is important. With $14,000 in premiums, that's definitely going to be noticed if they review your return.

I had some confusion with Form 4952 last year. Anyone know if tax software like TurboTax or H&R Block can handle this form correctly, especially the carryover calculations across multiple years?

This is a complex situation that many investors face when they discover investment interest deductions later. Let me add a few practical points that might help: First, before spending time and money on amendments, calculate whether the deductions would actually benefit you in those prior years. If you took the standard deduction and your total itemized deductions (including the investment interest) wouldn't exceed the standard deduction for those years, amendments won't help. Second, keep in mind that investment interest expense is subject to the 2% AGI threshold if you're dealing with years before 2018, which adds another layer of complexity to whether amendments are worthwhile. For your current year planning, since you're expecting substantial capital gains, consider the timing of your stock sales. You might benefit from spreading sales across tax years to optimize your investment income and better utilize any carried-forward deductions you can establish. Also, don't forget that investment interest expense includes more than just margin interest - it can include interest on loans used to purchase investment property, points paid on investment property loans, and other investment-related borrowing costs. Make sure you're capturing all eligible expenses in your calculations. The key takeaway is to start filing Form 4952 this year regardless of your prior year situation, so you don't face this documentation gap again in the future.