The community college near me offers free tax preparation through their accounting program! Students get real-world experience and you get free tax help - even with self-employment income! I'm SO ANGRY that the IRS and tax prep companies don't advertise these options more widely!!! Check your local community colleges, universities with accounting programs, or even law schools. Many have IRS-certified volunteer programs that can handle self-employment returns at no cost. You deserve access to free filing regardless of your income source!

I wish I had seen this thread earlier this tax season! As someone who just started freelance consulting work, I fell into the exact same trap - spent three weekends trying different "free" platforms only to hit paywall after paywall once I mentioned my 1099-NEC income. What's really frustrating is that the IRS's own Free File page makes it sound like there are plenty of options, but when you actually try to use them, it's a different story entirely. I ended up using Cash App Taxes based on a recommendation from another forum, and honestly, it worked better than I expected. The interface was clean, it walked me through all the Schedule C stuff without trying to upsell me, and both my federal and state returns were actually free. My only advice is to gather ALL your business receipts and expense documentation before you start - having everything organized made the process so much smoother. Thanks for sharing your experience - it's reassuring to know others have navigated this successfully!

One thing nobody has mentioned is that Missouri has some specific state-level considerations for S-corps that differ from some other states. I'm a MO agent too, and our state taxes S-corps a bit differently than sole props. Make sure whoever you work with is familiar with MO specifically. Also, did your CPA mention anything about how the 20% QBI deduction factors into this decision? That's another big piece of the S-corp vs LLC analysis that might affect your choice.

Great point about Missouri-specific considerations! The QBI deduction interaction is crucial and often overlooked. For S-corps, the QBI deduction applies to your business income MINUS the W-2 wages you pay yourself. So if you're paying yourself a high salary (like that 70% some CPAs recommend), you're reducing the income eligible for the 20% QBI deduction. This creates an interesting balance - you want your salary high enough to avoid IRS scrutiny but not so high that you lose significant QBI benefits. In many cases, this actually supports the 50-60% salary range that others have mentioned here. Missouri also doesn't conform to federal S-corp elections automatically, so you need to make a separate state election. Plus MO has that franchise tax for S-corps that LLCs don't pay. These state-level costs should definitely factor into your breakeven analysis. I'd recommend running the numbers with both federal AND Missouri tax implications included. The total picture might be different than just looking at federal savings alone.

@Liam McGuire - I just went through this exact decision process last month! The combination of student debt stress and stock grant confusion is rough, but you can definitely figure this out. Here's my practical approach: First, don't panic about the 30-day deadline - you still have time to get the right information. Email your HR team TODAY asking for: 1) The current 409A valuation per share, 2) Your exact number of shares, 3) Your exercise/strike price (if any), and 4) Whether this is an ISO, NSO, or RSU grant (the tax treatment differs slightly). While you're waiting for those numbers, think about your risk tolerance. Filing 83(b) is essentially making a bet that your company will grow significantly over the next 4 years. If you're at a very early-stage startup with lots of growth potential, it usually makes sense. If you're at a more mature company that's already highly valued, the benefits are smaller. Given your $42k in student loans, I'd suggest calculating what that immediate tax hit would mean for your monthly budget. If it's going to stress you out financially or delay your loan payments, that's a real cost to factor in too. Sometimes the peace of mind from better cash flow is worth more than potential tax savings. One last thing - if you decide to file, make sure you send it certified mail and keep copies. The IRS is strict about the 30-day deadline and proper filing procedures. Don't let a paperwork mistake invalidate your election!

@Liam McGuire - As someone who works in equity compensation at a tech company, I see employees struggle with this decision all the time. The good news is that your situation (early career, student debt, first stock grant) is actually pretty common and manageable. Here's what I tell everyone: the 83(b) decision comes down to three key factors - current valuation, growth expectations, and your personal cash flow. Since you mentioned this is part of a promotion package, I'm guessing your company values talent retention and likely has decent growth prospects. The student loan concern is totally valid, but remember that you're not committing to monthly payments - this would be a one-time tax event that you'd handle during your regular tax filing. If the current 409A valuation is low (which it often is for earlier-stage companies), your immediate tax hit might be surprisingly small - maybe $500-2000 depending on your grant size and company stage. My recommendation: Get those specific numbers from your finance team this week, then run a simple calculation. If the immediate tax cost is less than what you'd pay in student loan interest over 2-3 months, and you believe in your company's growth potential, filing 83(b) usually makes financial sense. Don't let fear of the unknown drive this decision - get the real numbers and then you can make an informed choice. You've got this!

I'm dealing with a very similar situation right now! Filed an extension, made an overpayment, then mailed my completed return in August with Form 8958 (also MFS in a community property state). USPS shows delivered but the IRS has no record of it. Reading through all these responses, I'm definitely going to try calling and asking specifically for "Accounts Management" - that tip about Form 8958 filings getting stuck in manual review makes perfect sense. I had no idea there were different departments with access to different systems. For what it's worth, I also tried the "Where's My Refund" tool online and it just says my information doesn't match their records, which is exactly what you'd expect if the return is sitting in some processing limbo. The frustrating part is that I'm also owed a refund (about $900) from my extension overpayment, so this delay is costing me money I could really use right now. But it sounds like once you get to the right department, they can actually resolve these issues pretty quickly. Thanks everyone for sharing your experiences - this thread has been way more helpful than the three different IRS reps I've spoken with so far!

This is such a frustrating situation, but you're definitely not alone! Based on what I'm reading here, it sounds like your return might be caught up in the same manual review process that affects a lot of MFS filers with Form 8958. A few additional thoughts that might help: - Keep detailed records of every phone call you make to the IRS, including date, time, rep name (if they give it), and what they tell you. This documentation will be crucial if you need to escalate later. - When you do get through to Accounts Management, ask them to put notes in your file about the missing return and the steps they're taking. This way if you have to call back, the next rep can see the history. - Consider also requesting a "wage and income transcript" while you're on the call - this will show if your employer's W-2 information matches what you filed, which can help rule out other processing issues. The good news is that since you have USPS tracking showing delivery, you should be protected from any late filing penalties even if this takes longer to resolve. The IRS generally accepts postal service delivery confirmation as proof of timely filing. Hang in there - it sounds like most people in this thread eventually got their situations resolved once they reached the right department. Your $1,400 refund is definitely worth the effort to track down!

Just wanted to add my experience as someone who went through this exact same situation two years ago. The stress you're feeling is totally understandable - that 1099-S form can be really intimidating when you see the full sale price listed! The good news is that since you lived in the house as your primary residence for over 2 years (you mentioned 7 years), you almost certainly qualify for the capital gains exclusion. With your gain around $85K, you're well under the $250K limit for single filers. One thing that really helped me was organizing all my documents beforehand. Make sure you have: - Your original purchase contract/closing statement - Records of any major improvements (new roof, kitchen renovation, etc.) - Your recent sale closing statement - The 1099-S form When I used the VITA program, I created a simple one-page summary showing: "Purchase price: $X, Sale price: $Y, Major improvements: $Z, Estimated gain: $A (under exclusion limit)." The volunteer preparer really appreciated having everything laid out clearly. Don't worry about the mortgage payoff amount shown on the 1099-S - that's totally normal and expected. The tax preparer will use your closing statement to calculate your actual proceeds and basis correctly. You're going to be fine!

I completely understand your stress about the 1099-S - I had the exact same panic when I sold my condo last year! The form showing the full gross proceeds is standard and doesn't mean you'll be taxed on that entire amount. Since you've lived there as your primary residence for 7 years and your actual gain is around $85K, you're definitely eligible for the capital gains exclusion (up to $250K for single filers, $500K for married filing jointly). The key is making sure your tax preparer understands this. Here's what I'd recommend for your VITA appointment: 1. Bring your original purchase closing statement to establish your cost basis 2. Include documentation of any major home improvements you made (these increase your basis and reduce taxable gain) 3. Your recent sale closing statement showing the mortgage payoff 4. Write a brief note explaining: "Primary residence for 7+ years, eligible for capital gains exclusion, actual gain approximately $85K" The volunteer preparers are trained to handle home sales, but that summary note will help ensure nothing gets missed. You're well under the exclusion threshold, so you shouldn't owe any tax on the sale. The 1099-S is just the IRS's way of tracking the transaction - your actual tax liability will be calculated correctly on Forms 8949 and Schedule D. You're going to be fine! This is a very common situation and the tax code is designed to protect homeowners in exactly your circumstances.