Just a heads up - if you decide to estimate your income, be VERY careful about tips. The IRS watches server income closely because underreporting tips is common. Remember that Denny's would have reported your credit card tips, and they've likely already submitted that info to the IRS.

Dylan, I went through this exact situation a few years back with a restaurant job! Here's what worked for me: First, try to reconstruct your income using any records you have - bank deposits, credit card statements showing tip deposits, even text messages about your schedule. For the W-2 issue, you have two main paths: 1) File Form 4852 with your best estimates, or 2) Try to get your wage transcript from the IRS first (either online or by calling). The transcript will show exactly what Denny's reported. One thing to keep in mind - restaurants are required to report all credit card tips to the IRS, so they definitely have records of at least that portion of your income. Your estimate needs to be reasonably close to what they reported, especially for tips. If you're running out of time before the deadline, don't panic about filing an extension (Form 4868). It gives you until October 15th to file, though you still need to pay any taxes owed by the original deadline to avoid penalties. The key is don't skip reporting this income entirely - that will cause bigger problems than filing with reasonable estimates and correcting later if needed!

Welcome to the community! I'm in a very similar situation - started playing social casinos about 6 months ago and now trying to navigate this tax maze. This thread has been incredibly educational. One thing I wanted to add based on my recent experience: when requesting transaction records from customer service, also ask specifically about their "coin conversion rates" if your platform uses multiple types of virtual currency. My platform has gold coins, sweep coins, AND bonus coins, each with different redemption rules. Understanding these distinctions helped me realize that some of my "big wins" were actually just bonus coins that can't be cashed out. Also, for anyone using multiple social casino platforms (like I do), make sure you're tracking each one separately. The tax reporting requirements are the same, but each platform has different policies about record retention and customer service responsiveness. I learned this the hard way when one platform was super helpful with detailed records while another basically told me to figure it out myself. The advice about starting fresh with better record-keeping for 2025 resonates strongly. I've set up a simple system where I take a screenshot before and after each session, and immediately log the key details in a shared Google Sheet that my spouse can access too (in case something happens to me). It takes literally 2 minutes but will save hours of reconstruction work next tax season. Thanks everyone for sharing your real experiences - it's so much more helpful than the generic tax advice you find elsewhere!

As someone who just discovered this community while frantically googling "social casino tax help," I can't thank everyone enough for this incredibly detailed discussion! I'm in almost exactly the same boat as the original poster - got into social casinos about 8 months ago and now staring down tax season with about $3,200 in cashouts and roughly $800 in coin purchases. Reading through all these experiences has been both reassuring and eye-opening. I had no idea about the sweep coin vs. gold coin distinction for tax purposes, or that I could request detailed transaction histories from customer service. I literally thought I was going to have to piece everything together from my credit card statements alone. The consensus seems crystal clear: report the cashouts as "Other Income" and don't try to hide anything from the IRS. The advice about checking whether itemizing actually makes sense versus taking the standard deduction is huge - I was automatically assuming I should try to claim my losses without doing the math on total deductions. I'm definitely going to contact my platform's customer service this week to get those complete records before they potentially get purged. And starting that screenshot + spreadsheet system for 2025 is now at the top of my to-do list. For other newcomers stumbling across this thread - the practical advice here is worth its weight in gold. Thanks to everyone who shared their real experiences dealing with this relatively new tax situation. It's clear this community really looks out for each other!

Anyone else notice that TurboTax mobile app doesn't support all the same forms as the desktop version? I tried using it last year for my side business and had to switch back to desktop for Schedule C. Has this been fixed in the newest version?

I'm in a similar situation - had to sell my laptop last year and now only have my iPhone and iPad. I've been using TurboTax Online (the web version) through Safari on my iPad for the past two years and it's worked great for my situation with mortgage interest, student loan interest, and charitable deductions. The key thing is to make sure you choose TurboTax Online, not try to download the desktop software. The online version has all the same features as the desktop version - I've compared my returns from when I had a laptop and the deductions found were identical. One tip: keep all your tax documents in your Photos app or a cloud service so you can easily access them while filling out forms. The iPad screen is plenty big enough to have the tax form open while referencing your documents. I actually prefer it now to the desktop experience!

Congratulations on your incredible win, Miguel! A 2025 Lexus is absolutely amazing - what a life-changing moment that must have been! I haven't been through this exact situation myself, but reading through everyone's experiences and advice here has been so educational. It sounds like you've gotten some really solid guidance about the tax implications and strategic options to consider. A few questions for those who have been through similar situations: 1. **Insurance shopping** - For those who won cars, did you find that some insurance companies were better than others at handling high-value vehicles that were prizes? I'm wondering if the "acquisition cost" being essentially zero affects how they calculate premiums. 2. **Maintenance considerations** - Beyond the higher insurance costs everyone mentioned, are there other ongoing ownership costs that might be different for a luxury car versus a regular vehicle? Things like specialized maintenance requirements or parts costs? 3. **Documentation for the IRS** - If Miguel does pursue getting the prize value re-appraised or documents that the fair market value is lower than stated, what kind of documentation would be most compelling to the IRS? Professional appraisals? Comparable sales data? It's really encouraging to see how this community comes together to help someone navigate such a complex but ultimately positive situation. Miguel, it sounds like you're approaching this really thoughtfully and asking all the right questions. Even with all the tax planning required, you're still coming out incredibly far ahead! Looking forward to hearing how your conversations with the sweepstakes company go regarding timing and potential cash options.

Wow Miguel, congratulations on winning that Lexus! What an incredible stroke of luck! I can totally understand the mix of excitement and anxiety you must be feeling right now. Reading through all the amazing advice everyone has shared here, it really sounds like you're getting some solid guidance on navigating this complex but ultimately wonderful situation. The suggestions about timing flexibility, getting independent appraisals, and exploring partial cash options all seem like really smart strategies to pursue. One thing I wanted to add that I don't think has been mentioned yet - if you do decide to keep the car, you might want to consider whether your current living situation can accommodate a luxury vehicle. Things like whether you have secure parking, if you live in an area with high theft rates for luxury cars, or if you frequently drive in conditions that might not be ideal for a brand new Lexus (like areas with lots of road salt in winter, heavy construction zones, etc.). These factors won't affect your taxes, but they could impact your insurance rates and the long-term value retention of the vehicle. Some people find that winning a high-end car actually changes their lifestyle in ways they weren't expecting - like feeling anxious about parking it in certain areas or worrying about door dings. That said, even with all these considerations, you're still in an absolutely amazing position! A tax bill of $12k-15k for a $45k car is still an incredible deal. I'm really curious to hear how your conversations with the sweepstakes company go about timing and cash alternatives. Thanks for sharing your situation - it's been really educational for all of us!

This is such a complex situation! I went through something similar when my spouse and I had jobs in different states. One thing that really helped us was keeping detailed records of everything - days spent in each state, where we voted, which state our driver's licenses were in, etc. The employment situation with your wife potentially switching from salary to contract work is interesting - that could actually impact the tax analysis significantly since contract income is treated differently than W-2 income for state tax purposes. You might want to run the numbers both ways (her staying salaried in NJ vs. becoming a contractor) to see which scenario is more tax-advantageous overall. Also, don't forget about things like voter registration and car registration - these can be factors that states use to determine your "true" domicile if there's ever a question. Make sure whatever you choose is consistent across all your official documents.

As someone who's dealt with multi-state tax situations, I'd strongly recommend getting professional help early in the process rather than trying to figure this out on your own. The interplay between federal filing status, state residency rules, and employment classification can get incredibly complex. A few specific things to consider for your situation: 1. **Timing matters**: Since you're moving in April, you'll need to track exactly when you establish Colorado residency (often based on when you get a CO driver's license, register to vote, etc.). This affects your partial-year resident status in both states. 2. **Your wife's employment status**: If she switches to contract work, she'll need to pay self-employment taxes AND deal with quarterly estimated payments. This could significantly impact your cash flow and overall tax burden compared to staying on salary. 3. **Reciprocity agreements**: Check if NJ and CO have any tax agreements that might simplify your filing requirements or prevent double taxation on certain types of income. 4. **School district implications**: Since your daughter is finishing the school year in NJ, make sure your residency decisions don't inadvertently affect her enrollment status or create issues for next year in Colorado. I'd suggest consulting with a CPA who specializes in multi-state taxation before making any final decisions about filing status or your wife's employment classification. The upfront cost could save you thousands in the long run.