Its way too early to worry tbh. The IRS is still processing returns from last year lmaooo 🤡

Same thing happened to me last year! The SBTPG portal doesn't populate until the IRS actually starts processing your refund for payment. Since you just filed last week, you're still well within the normal timeframe. I'd give it another week or two before getting concerned. The "accepted" status just means they received it without errors, but processing takes time especially early in the season.

Don't panic about the missed June payment! The IRS isn't as scary as everyone makes them out to be. I missed TWO quarterly payments last year when I switched from W2 to freelancing and the penalty was only like $75 when I filed. The most important thing is to start making payments now for September and January. You can easily do this online at IRS.gov using Direct Pay - takes like 5 minutes. And definitely dont worry about "bothering" your accountant. That's literally his job! Even if it's his off season, he should at least respond to urgent questions. If he won't, might be time to find someone new.

I've been freelancing for about 3 years now and can share some practical advice from my experience: For your first question - yes, definitely start making quarterly payments now. The general rule is if you expect to owe $1,000+ in taxes when you file, you need to make estimated payments. Regarding the June deadline - don't stress too much about it. The penalty is calculated as a percentage (currently around 8% annually) of the underpaid amount for the time it was late. So if you owe $2,000 for that quarter and pay it 2 months late, you're looking at maybe $25-50 in penalties, not hundreds. One thing that really helped me was using the "safe harbor" rule - if you pay 100% of what you owed last year (or 110% if your prior year AGI was over $150k), you won't face any penalties even if you end up owing more when you file. This gives you a baseline to work with. For tracking, I highly recommend QuickBooks Self-Employed or even just a dedicated business bank account like others mentioned. Makes everything so much cleaner at tax time. And honestly, if your tax guy disappears completely during off-season, that's a red flag. A good tax professional should at least be available for urgent questions year-round, even if they're busier in spring.

This is a really complex QSBS situation that requires careful planning. One additional consideration I haven't seen mentioned yet is the working capital safe harbor under 1202(e)(6). When you're contributing assets from the 3 C Corps to the new corporation, you'll want to ensure that any cash or investment assets don't push you over the limits for qualifying as an active business. The safe harbor allows reasonable amounts of working capital, but "reasonable" is based on the business needs and plans of the company. If the C Corps are contributing significant cash along with equipment, you might need to document specific business plans for how that working capital will be used in the active business within 2 years. Also, regarding the LLC conversion timing - make sure you're structuring this so the converted C Corp is the one receiving the contributed assets, not doing the contributions first and then converting. The order of operations could affect whether the resulting stock qualifies under Rev Rul 84-111. Have you considered getting a private letter ruling for this structure? Given the complexity and the multiple moving parts, it might be worth the cost and time to get IRS blessing upfront rather than risking an audit challenge later.

The complexity of your situation definitely warrants careful structuring. One approach that might work is to treat this as two separate phases: first, complete the LLC-to-C-Corp conversion under Rev Rul 84-111 to establish your qualifying QSBS entity. Then, after sufficient time has passed (ideally 60-90 days to avoid step transaction issues), liquidate the 3 C Corps and have their shareholders contribute the assets directly to the converted corporation. This structure should help you avoid the stock-for-stock exchange prohibition in 1202(c)(1)(B) since the shareholders would be contributing assets, not stock. The liquidation gives them a stepped-up basis in the distributed assets, which addresses the basis reference concerns under 1202(h)(2). However, you'll need to be very careful about several things: (1) ensure the converted C Corp meets the $50M gross assets test after receiving the contributed assets, (2) document legitimate business purposes for each transaction step, (3) verify that any cash contributions fit within the working capital safe harbor, and (4) make sure no redemptions occur within the prohibited 4-year window. Given the potential tax savings at stake and the multiple compliance requirements, I'd strongly recommend getting a private letter ruling. The cost is usually justified when you're dealing with this level of complexity and the potential for significant QSBS benefits.

This has been such a helpful thread! I'm in a similar boat - first time using a professional preparer after years of doing my own taxes with TurboTax. My situation got complicated with some freelance income and I was totally lost. My preparer was amazing and found several business deductions I had no clue about. I was definitely thinking about tipping since that's my instinct when someone provides great service, but reading all these responses from actual tax professionals really opened my eyes. I love the idea of a coffee shop gift card - that feels like the perfect middle ground between showing appreciation and staying professional. And I definitely need to write a detailed Google review. She spent almost an hour explaining estimated quarterly payments to me which probably saved me from underpayment penalties next year. Thanks everyone for the education on proper etiquette here! It's so different from other service industries but makes total sense.

As a tax professional myself, I really appreciate this whole discussion! It's refreshing to see people wanting to show appreciation appropriately. The gift card to a local coffee shop is honestly perfect - we absolutely run on caffeine during tax season and it shows you put thought into something we'd actually use. The $25-50 range mentioned earlier is spot on. But I have to echo what others have said - detailed Google reviews are pure gold for us. When you mention specifics like "found business deductions for my freelance work" or "explained quarterly estimated payments," that tells future clients exactly what kind of expertise we offer. Those reviews bring in clients who are actually a good fit for our services. One more thing - if your preparer offers year-round tax planning consultations (many of us do), that's another great way to show appreciation. Coming back for mid-year check-ins or planning sessions shows you value the relationship beyond just the annual filing. Plus it often saves you money in the long run!

I went through this exact situation in 2023 and want to offer some reassurance - you're absolutely right that you shouldn't owe taxes on personal items sold at a loss! The most important thing to understand is that the 1099-K is just eBay's report to the IRS of gross payments processed - it doesn't determine your actual tax liability. Since you sold personal belongings at a loss, you have no taxable gain to report. Here's the approach that worked best for me after consulting with multiple sources: Report the 1099-K on Schedule 1, Line 8z (Other Income) with a description like "Personal items sold at loss - eBay 1099-K." Then document your cost basis (what you originally paid) for each item. For documentation, I created a simple spreadsheet with three columns: Item Description, Original Cost, and Sale Price. For items without receipts, I used reasonable estimates based on what I remembered paying or looked up similar retail prices online. The IRS accepts good faith estimates for personal property - they understand people don't keep receipts for everything. Since your total original costs will likely exceed your sales proceeds, you can show zero taxable income while still accounting for the 1099-K the IRS received from eBay. Don't stress too much about perfect documentation. Focus on being transparent about the transactions and showing that these were personal items sold during financial hardship, not business inventory sold for profit. The IRS encounters this situation frequently and has guidance specifically addressing personal property sales. You're being proactive by researching this properly - that's exactly the right approach!

I'm dealing with a very similar situation right now and this thread has been incredibly helpful! I received a 1099-K from eBay after selling my old gaming console, some furniture, and various household items during a tough financial period last year. Like you, I definitely sold everything for less than what I originally paid. After reading through all the advice here, I'm planning to use the Schedule 1, Line 8z approach that several people have recommended. It seems like the clearest way to show the IRS that I received the 1099-K they have on file while demonstrating that there was no actual taxable gain from these personal item sales. I'm creating a spreadsheet documenting what I originally paid for each item versus what I sold it for. Even though I don't have receipts for everything, I can make reasonable estimates based on what I remember paying or by looking up similar items online to estimate original retail prices. The reassurance from multiple people here that the IRS understands people sometimes need to sell personal belongings during financial hardship really helps reduce the stress. It's comforting to know this is a common situation that many people navigate successfully each tax season. Thanks for starting this discussion - it's exactly the kind of practical guidance those of us in this situation need to hear!