Just want to add a practical tip that saved me a lot of headache when I went through this exact situation last year - document everything about the working relationship from day one! Keep records of the training you provide, any performance evaluations, work schedules, and how you direct their daily tasks. If the IRS ever questions the classification, having clear documentation showing the level of control and direction you provided will support your W-2 decision. Also, since everyone's mentioning the multi-state complexity - one thing that caught me off guard was that some states require you to post specific labor law notices even for remote workers. Make sure to check if the intern's state requires you to provide digital copies of workplace rights posters or other notifications, even though they're working remotely. It's a small detail but can avoid compliance issues down the road. The consensus here is absolutely right though - with set hours, training, and working on core business projects, this is definitely W-2 territory regardless of the remote/temporary nature.

@Fatima Al-Hashemi - Great question about checklists! I actually created a comprehensive checklist after going through this process myself. Here are the key documentation areas you'll want to cover: **Pre-hiring:** - Job description showing level of supervision/training - Interview notes about work arrangement expectations - Signed offer letter outlining W-2 status **During employment:** - Training records and materials provided - Work schedules and time tracking - Performance feedback/evaluations - Communications showing work direction - Any company equipment provided - Records of company meetings/training attended **State compliance (varies by state):** - Digital labor law posters sent to remote workers - Workers' compensation notifications - State-specific new hire reporting - Unemployment insurance registration confirmations **Tax/payroll:** - Completed W-4 and I-9 forms - Payroll records with proper tax withholdings - State tax registration documents The Department of Labor website has some good templates for employment documentation, and most payroll services like Gusto will provide checklists for their specific platform. I'd also recommend touching base with an employment attorney or HR consultant for your first intern - the upfront investment in getting the process right will save you so much stress later! The labor poster requirements really vary by state, so definitely check with your payroll service about what's needed for remote workers in your intern's specific location.

I'm completely new to both this community and the gig economy world, so thank you all for breaking down the processing date confusion! As someone who just filed their first tax return as a freelancer, I've been absolutely lost trying to understand what my transcript was telling me. I was definitely making that same mistake of thinking the processing date was like a countdown timer to when my refund would arrive - I've been checking it multiple times a day hoping to see some magical change! 😅 Learning that it's basically just a "last updated" timestamp makes so much more sense, even though it's frustrating that the IRS couldn't just call it that. The stress of waiting for this refund as a new gig worker is so real when you're counting on that money for bills. I had no idea tax transcripts were even a thing until I started researching why my refund was taking longer than expected! This community has already been such a lifesaver for getting actual human explanations instead of trying to decode the IRS website alone. The advice about focusing on "Where's My Refund" instead of trying to interpret every single code is exactly what I needed to hear. Thanks to everyone sharing their experiences - it's incredibly reassuring to know this confusion is totally normal! 🙏

As someone who's completely new to this community and the freelancing world, this thread has been an absolute lifesaver! I just started doing gig work this year and honestly had no clue what I was looking at when I first pulled up my tax transcript. The processing date confusion is SO real - I've been checking it obsessively thinking it was telling me when my refund would actually arrive! 😅 Learning that it's basically just a "last updated" timestamp rather than any kind of promise about timing makes so much more sense, even though it's incredibly frustrating that the IRS couldn't just use clear language in the first place. As a newcomer to gig work, the financial stress of waiting for this refund is definitely real when you're counting on that money for upcoming bills. I had no idea tax transcripts were even a thing until I started researching why my refund was taking longer than the "21 days" they mention everywhere. The advice everyone's shared about focusing on the "Where's My Refund" tool instead of trying to decode every single transcript code has already saved my sanity! It's wild that in 2025 we need an entire community just to translate what should be basic information about our own tax returns, but I'm so grateful this place exists. Thanks to everyone who's shared their experiences - it's incredibly reassuring to know this confusion is completely normal and that most people do eventually get their refunds even when the whole system makes it feel like absolutely nothing is happening! 🙏

I'm sorta confused why the IRS would send a 1099-INT in the first place? Like, they're the ones who process our tax returns, so can't they just automatically account for this interest they paid us?

The 1099-INT from the IRS is definitely just reporting interest they paid you on a delayed refund - it's pretty common when refunds take longer than 45 days to process. You're right that you don't need to "fill it out" - it's just an informational document showing taxable income you received. In TurboTax, go to the Federal Taxes section, then Income & Expenses, and look for "Interest and Dividends." Enter the information from your 1099-INT there - the payer will be "Internal Revenue Service" and the amount will be whatever's shown in Box 1 of the form. And definitely ignore anything about Form 1096 - that's only for businesses that are sending information returns TO the IRS, not for individuals receiving them. The fact that you can't print it is actually irrelevant since you don't need it anyway! This interest is taxable income, so it will add a small amount to your tax liability, but it's straightforward to report. Don't stress about it - the IRS already knows they paid you this interest, so as long as you report it correctly on your return, you'll be fine.

This thread has been incredibly helpful! I was pulling my hair out over the same issue with my Schwab 1099-B. I kept seeing gain/loss calculations right there on the form but getting warnings about missing cost basis info. After reading through everyone's explanations, I finally understand that it's all about what gets reported to the IRS versus what the brokerage shows me. The key insight about checking the "Cost Basis Reported to IRS" column on the 1099-B is gold - I wish they made that more obvious! For anyone else dealing with this, I found that most of my "non-covered" transactions were from stock purchases I made back in 2009-2010 (before the reporting requirements kicked in) and some transfers from an old Merrill account. Makes total sense now why those would need code B on Form 8949 even though Schwab calculated the gains correctly on my form. One thing I'd add is that if you're using tax software, double-check that it's not automatically importing these as "covered" transactions. I caught TaxAct trying to treat everything as if it was reported to the IRS, which would have been wrong for about half my trades.

I've been dealing with this exact same confusion for years and finally have a system that works! What really helped me was creating a simple spreadsheet to track the status of each transaction before tax season even starts. Here's what I do: Every time I sell something, I immediately check Fidelity's "Positions" page to see if that security shows up as "covered" or "non-covered" for cost basis reporting. I log this in my spreadsheet along with the basic transaction details (date sold, proceeds, my calculated gain/loss). Then when my 1099-B arrives, I can quickly cross-reference my spreadsheet against the "Cost Basis Reported to IRS" column to make sure everything matches up. Any "No" entries in that column go straight to the "needs code B on Form 8949" pile. This has saved me so much stress during tax season because I'm not scrambling to figure out which transactions are causing the "missing cost basis" warnings. Plus it helps catch any discrepancies between what I calculated during the year versus what shows up on the actual 1099-B. The whole system takes maybe 5 minutes per transaction when I sell, but saves hours of confusion in March/April!

This discussion has been incredibly enlightening! As someone who's been contemplating the exact same LLC vs Schedule C decision for my sports betting income, reading everyone's real-world experiences has been invaluable. What really struck me is how the fundamental mechanics of sportsbook operations (SSN reporting, no business accounts allowed) create insurmountable obstacles for legitimate business entity treatment. I had been so focused on the potential SE tax savings that I wasn't fully considering how difficult it would be to justify the structure if audited. The consensus seems clear: the administrative burden, audit risk, and questionable defensibility of transferring personally-earned income to business accounts far outweigh the modest tax savings. Plus, as several people calculated, the actual SE tax benefits after reasonable salary requirements and additional costs are much smaller than they initially appear. I'm particularly grateful for the specific deduction suggestions and documentation strategies for maintaining professional gambler status. The key insight about the "facts and circumstances" test focusing on systematic approach rather than income percentage gives me confidence that professional status can be maintained even as betting becomes secondary income. One question for those who've gone the Schedule C route: how do you handle the timing of income recognition? Since sportsbooks issue 1099s that might not align perfectly with your actual betting activity patterns, do you use cash or accrual method, and have you run into any reconciliation issues during filing?

This entire discussion has been a masterclass in sports betting tax strategy! As someone who's been making similar income from DraftKings and FanDuel ($75k+ annually), I was heading down the exact same LLC path until reading all these real-world experiences. The point about sportsbooks requiring SSN reporting really is the fatal flaw in the LLC approach. I hadn't fully grasped how that creates an impossible paper trail to defend - you're essentially trying to argue that personally-earned, personally-reported income is somehow business income just because you transfer it to a business account afterward. What's been most valuable is seeing the actual numbers people calculated for SE tax savings. When you factor in reasonable salary requirements, payroll processing, additional filing costs, and LLC maintenance fees, those theoretical savings shrink dramatically. The $3,000-4,500 annual benefit mentioned earlier really puts it in perspective - not worth the complexity and audit risk. I'm convinced that the Schedule C professional gambler route is the way to go. The systematic documentation approach several people described (detailed time tracking, expense categorization, business-like record keeping) seems to provide the same tax benefits without the structural complications. One follow-up question: for those tracking "substantial time investment" to maintain professional status, what specific activities do you log beyond just the actual betting? I'm thinking research time, odds analysis, bankroll management, etc. - but want to make sure I'm capturing everything that legitimately supports the professional classification. The peace of mind factor really resonates too. Having a clean, defensible position aligned with how the income actually flows seems much better than trying to force a square peg into a round hole just for modest tax optimization.