Based on your situation, you're handling this correctly with the sessions method. You should report the $815k in winning sessions as gambling income and deduct the $246k in losing sessions on Schedule A - not your total individual transaction losses of $3.1m. The sessions method requires consistency throughout your entire approach. Since you've calculated your gambling activity using daily sessions (which is the standard approach for online platforms like FanDuel), you must stick with those session totals for both income reporting and loss deductions. A few important considerations for your specific case: 1. **Documentation is critical** - Keep your FanDuel transaction exports, your session calculation spreadsheets, and clear notes on your methodology. Define exactly how you determined each session (likely by calendar day) and apply it consistently. 2. **Tax software limitations** - H&R Block may try to default to reporting your full W-2G amounts. You'll likely need to override this and manually enter your session-calculated figures with proper documentation. 3. **State tax implications** - Double-check how your state handles gambling income. Some states don't recognize the sessions method and may require you to report the full W-2G amounts, which could significantly impact your state tax bill. 4. **Professional review recommended** - Given the substantial amounts involved ($290k federal tax liability), consider having a tax professional who specializes in gambling taxes review your calculations before filing. The upfront cost could save you significant problems if the IRS has questions later. The sessions method is well-established in tax court precedent and is designed to reflect the economic reality of continuous gambling activity. Just ensure your documentation clearly supports your methodology and calculations.

The sessions method approach you're using is definitely the correct way to handle this situation. Your calculation of $815k in winning sessions as reportable income and $246k in losing sessions as your deductible losses is spot-on. What many people miss is that the sessions method isn't just about reducing taxes - it's about accurately reflecting the economic reality of your gambling activity. When you're making continuous bets on FanDuel throughout a day, each individual transaction doesn't represent a complete gambling event. The session as a whole does. A few key points for your situation: **Federal reporting**: Report the $815k as "Other Income" on Schedule 1 and deduct the $246k as gambling losses on Schedule A (subject to itemizing). You cannot mix methodologies by using session income but total transaction losses. **Record keeping**: Make sure you have clear documentation of how you defined each session (most likely by calendar day for online betting) and that you applied this consistently throughout 2023. Keep your FanDuel transaction exports and any spreadsheets showing your calculations. **Software considerations**: Tax software often defaults to W-2G amounts, so you may need to override these entries manually. Include a statement explaining your sessions methodology and reference supporting tax court cases like Mayo v. Commissioner. The $290k federal tax bill you're seeing is based on legitimate gambling income under an accepted methodology. While painful, it's much better than the alternative of reporting the full $2.3m in W-2Gs without proper session accounting. Consider having a tax professional who specializes in gambling taxes review everything before filing, especially given the substantial amounts involved.

I'm in a similar situation - just finished my EMT-B certification last month and was really hoping to deduct those costs too. One thing I discovered is that some volunteer fire departments will cover certification costs if you commit to volunteering for a certain period. Might be worth looking into if you're open to volunteer work while job hunting. Also, keep all your receipts organized anyway - tax laws can change and you never know if there might be future opportunities to claim these expenses retroactively.

This is frustrating but unfortunately accurate info from Javier. I went through something similar when I got my nursing certifications a few years back - had to pay out of pocket for everything and couldn't deduct any of it. One thing that might help is looking into whether your state offers any tax credits specifically for first responders or healthcare workers. Some states have been adding these in recent years. Also, if you end up working for a municipality or government agency, they sometimes have tuition reimbursement programs that could help with future training costs. Keep pushing forward though - the investment will pay off in the long run even without the tax break!

Wait I'm confused about something. If I'm a substitute teacher working directly for a school district, wouldn't I be a W-2 employee not a 1099 contractor? I subbed last year and got a W-2.

Great question! As others have mentioned, you should receive a 1099-NEC from the learning center if they paid you $600 or more. But here's something important to keep in mind - the classification itself matters a lot. If the learning center was controlling your schedule, providing lesson plans, telling you exactly how to teach, or treating you like other employees, you might have been misclassified. True independent contractors have more control over how they do their work. This is especially common in education where companies try to avoid paying employment taxes and benefits. If you believe you were misclassified, you can file Form SS-8 with the IRS to get an official determination, or Form 8919 when you file your taxes to pay only the employee portion of Social Security and Medicare taxes instead of the full self-employment tax. This could save you money since self-employment tax is about 15.3% versus 7.65% for employees (the employer pays the other half). Just something to consider as you're navigating this for the first time!

This is absolutely heartbreaking, and I can only imagine the panic you felt seeing that negative balance when you're just trying to buy diapers for your kids. The "locust swarm" comparison really hits home - it's that complete devastation feeling. I went through something similar with Michigan Department of Treasury a few years back, and here's what I learned that might help: **Call Wisconsin DOR Collections IMMEDIATELY** - Don't wait another day. The number everyone's mentioned (608-266-7879) is correct. When you call, use these exact phrases: - "I'm requesting an immediate financial hardship review" - "I have two minor dependents with no means for basic necessities" - "I'm requesting a partial levy release under emergency hardship provisions" **Address Change Documentation** - This is HUGE. Wisconsin has a duty to make reasonable efforts to locate you before taking collection action. Gather: - All lease agreements/moving records from the past 6-9 years - Any mail forwarding confirmations - Proof you were never properly served notice **The 21-day window is critical** - Your bank mentioned 21 days before final transfer. This gives you time to file an emergency motion, but you need to act NOW. One thing that worked for me was emphasizing the immediate harm to my children. Tax authorities often have more flexibility when minor dependents are involved, especially for basic necessities like food and diapers. Also, document EVERYTHING from your calls - names, times, reference numbers. This paper trail becomes important if you need to escalate or file appeals. You're not powerless here, even though it feels like it. Many people have successfully gotten partial releases in similar situations. Stay strong! 💪

James, I'm so sorry you're dealing with this nightmare situation. As a single parent myself, I can't imagine the panic of trying to buy diapers and having your card declined when you know there should be money there. Here's what I'd recommend based on my experience with state tax issues: **Immediate Action Plan:** 1. Call Wisconsin DOR Collections at 608-266-7879 TOMORROW morning at 7:45 AM sharp (they open early and you'll have better luck getting through) 2. Have your SSN, account information, and dependent documentation ready 3. Request an "Emergency Financial Hardship Review" - use those exact words **Key Points to Emphasize:** - You have two minor dependents with immediate needs (food, diapers) - Your address changed multiple times and you received NO notice - This levy has left you unable to provide basic necessities for your children - Request immediate partial release for essential living expenses **Documentation to Gather Today:** - Proof of your dependents (birth certificates, tax returns) - Evidence of address changes (leases, utility bills, mail forwarding) - List of essential monthly expenses for your family Wisconsin does have provisions for emergency hardship situations, especially when children are involved. The fact that you never received proper notice due to address changes could also be grounds for challenging the levy entirely. Don't give up - many parents in similar situations have gotten partial releases within 24-48 hours when they emphasize the immediate impact on their children. You've got advocates here rooting for you! Keep us updated on how the call goes tomorrow. We're here to help! 💙

Don't forget that healthcare.gov specifically wants your PROJECTED annual income, not just what you've made so far. If you make $3,000 in profits over 3 months, they don't just want to see that - they want to see that projected to $12,000 for the year (assuming steady income). One mistake I made was just submitting my year-to-date income without the annual projection. My documentation kept getting rejected until I explicitly showed the math for how my partial-year income translated to an annual estimate.

For your inventory issue specifically - you're right to think about including that $650 in inventory value. Since you're in a buy/repair/sell business, that inventory represents future income that should be part of your annual projection. The key is to be consistent with your accounting method. If you've been using cash basis (only counting money when it actually comes in/goes out), then your inventory should be valued at what you paid for it, not what you expect to sell it for. If you switch to accrual accounting, you'd count the expected sale value, but then you'd also need to account for all your other income and expenses on an accrual basis. For healthcare.gov documentation, I'd recommend sticking with cash basis but including a line item like "Current inventory at cost: $650 - represents X units expected to generate approximately $Y in future sales over next Z months." This shows them you understand your business has ongoing value beyond just completed transactions. Also make sure your ledger clearly states the time period covered and includes your methodology for the annual projection. Something like "Income projection based on [method] - estimated annual net profit: $X" helps prevent the vague rejection letters you've been getting.