I went through this exact situation last year with about $2,800 in Bovada winnings. After doing a lot of research and talking to a tax professional, I can confirm that yes, you absolutely need to report those winnings as income. The key thing to understand is that the IRS requires you to report ALL income from gambling, regardless of whether you receive a tax form or not. The fact that Bovada operates offshore and doesn't issue W-2G forms doesn't change your legal obligation to report the income. Here's what I learned about the practical side: - Report the winnings on Schedule 1 as "Other Income" - If you itemize deductions, you can deduct losses up to the amount of your winnings on Schedule A - Keep detailed records of all your gambling activity (Bovada lets you download transaction history) - Document each gambling session with dates, amounts wagered, and results The $3,200 you mentioned is definitely significant enough that you should report it. Even though the IRS might not immediately know about offshore gambling winnings, they can spot patterns in your bank deposits that might trigger questions later. It's much better to be proactive and report everything correctly from the start. One tip: organize your transactions by individual gambling sessions rather than just total wins/losses for the year. This can help maximize your deductions if you itemize.

I just wanted to share my experience as someone who went through this exact situation. I had about $4,500 in Bovada winnings last year and was really unsure about reporting them. After consulting with a CPA who specializes in gambling taxes, here's what I learned: You definitely need to report ALL gambling winnings, even from offshore sites like Bovada. The IRS considers all gambling income taxable regardless of the source or whether you receive forms. I reported mine on Schedule 1 as "Other Income." The tricky part is documentation. Since Bovada doesn't send tax forms, you need to be extra diligent about record-keeping. I downloaded my complete transaction history from Bovada (available in your account settings) and organized it by gambling sessions. This helped me properly calculate my deductible losses to offset some of the winnings. One thing that really helped was keeping a simple spreadsheet throughout the year tracking each session - date, game type, starting amount, ending amount, and net result. It made tax time much easier and gave me confidence that I had proper documentation if ever audited. The peace of mind of doing everything correctly is worth way more than any tax you might save by not reporting. Plus, if you have losses (which most gamblers do), you can deduct those up to your winnings if you itemize, which can significantly reduce your tax burden.

Just a heads up to the original poster - be aware that if you do file as married (common law or otherwise), you'll need to continue filing that way unless you legally separate or divorce. That's true even for common law marriages - you can't just go back to filing single next year if you decide the tax benefits aren't worth it! Common law divorce isn't really a thing in most places - you'd need to go through regular divorce proceedings just like formally married couples. So make sure you're ready for that commitment before changing your filing status!

This is really helpful information! I'm actually in a similar situation in Colorado with my partner of 2.5 years. We've been hesitant to file jointly because we weren't sure if we'd need some kind of official paperwork first. One thing I'm curious about - if we start filing as married jointly this year, does that create any kind of official record of our common law marriage with the state? Or is it purely for federal tax purposes? I'm wondering if filing jointly would affect things like health insurance through employers, since some companies require proof of marriage for spousal coverage. Also, has anyone here ever been asked to provide documentation during an actual audit? I'd love to know what kinds of evidence the IRS typically looks for to verify common law marriage status.

I've been carrying forward capital losses for years and an important tip is to KEEP DETAILED RECORDS of all your previous tax returns. The IRS randomly decided to question my loss carryforward in 2023 and I had to provide proof from returns going back to 2019. Was a total nightmare trying to find all those documents.

One thing I'd add to the excellent advice already given - make sure you understand the "wash sale" rules before filing those back returns. If you sold crypto or stocks at a loss and then bought the same or "substantially identical" securities within 30 days before or after the sale, the IRS considers it a wash sale and you can't claim the loss immediately. This is especially tricky with crypto since many people were buying/selling frequently during those volatile periods in 2021-2022. The wash sale rules can significantly reduce your claimable losses, so it's worth double-checking your transaction history before you file. Some of the tax software mentioned earlier should catch this automatically, but it's good to be aware of the rule going in.

One additional consideration that hasn't been mentioned - if you're planning to move closer to your new job, make sure you understand the timing requirements for the Section 121 exclusion. You need to have used the home as your primary residence for at least 2 of the 5 years before the sale. Since you've lived there for 5 years already, you have some flexibility. But if you rent it out for 2 years and then sell, you'll be right at that 5-year lookback period. If for any reason the sale gets delayed (market conditions, finding buyers, etc.), you could potentially lose eligibility for the exclusion. Also, consider whether renting it out for just 2 years makes financial sense after factoring in landlord responsibilities, potential vacancy periods, property management costs, and the tax complexity it creates. Sometimes the headache isn't worth the extra income, especially if you're not planning to be a long-term landlord. You might want to run the numbers on selling now versus the rental income minus all associated costs and taxes.

Great discussion everyone! I'm actually a tax professional and wanted to add a few clarifications to help @Melina Haruko and others in similar situations. First, the Section 121 exclusion is indeed available as long as you meet the 2-out-of-5-year test, but there's an important nuance: if you claim depreciation during the rental period (which you're required to do), that portion of the gain will be subject to depreciation recapture at 25%, even if you qualify for the exclusion on the remaining gain. Second, regarding the tools and services mentioned - while they can be helpful, I'd strongly recommend consulting with a tax professional for your specific situation, especially given the complexity of partial-use properties. The IRS rules around this are quite detailed and small mistakes can be costly. Finally, @Zara Rashid made an excellent point about timing. Consider not just the tax implications, but also the practical aspects: property management from a distance, market timing risks, and whether the net rental income (after all expenses and taxes) justifies the complexity. Sometimes the cleanest financial move is to sell before converting to rental property. Feel free to ask if you have specific questions about the tax calculations!

Carmen, you're definitely not alone in feeling overwhelmed by delivery driver taxes! I just went through this same learning curve last year. One thing I'd add to all the great advice here is to start tracking your income and expenses RIGHT NOW, even if tax season feels far away. I made the mistake of trying to reconstruct everything from memory and bank statements later - it was a nightmare. Create a simple spreadsheet or use an app to log your daily earnings and any business expenses as they happen. Also, since you mentioned you're doing this mostly on weekends, make sure to track those miles even if it feels like "just" weekend work. Weekend driving often means longer distances to busier areas, so those miles really add up! And don't stress too much about getting everything perfect your first year. The IRS understands that gig work is new for a lot of people. Just keep good records and be honest about your income and legitimate business expenses. You've got this!

Carmen, I totally feel your stress about this! I was in the exact same boat when I started doing delivery work. Here's my simplified breakdown for getting started: **Immediate action items:** 1. Download a mileage tracking app TODAY (Stride, MileIQ, or even Google Maps timeline) 2. Start a simple expense log - even just notes in your phone 3. Open a separate savings account and put 25-30% of each week's earnings in there **What you CAN deduct:** - All business miles (including driving to hotspots, between deliveries, etc.) - Hot bags, phone mount, car charger - Portion of phone bill (maybe 20-30% if used primarily for work) - Car washes if done specifically for delivery work - Hand sanitizer, tissues, other supplies **Forms you'll need:** - 1099-NEC from Uber (if you make over $600 total) - Schedule C for your tax return - Form SE for self-employment tax The biggest mistake I made my first year was not tracking miles from day one. Don't be like me! Even if you only work weekends, those miles to busy areas really add up. And remember - you're learning, and that's okay. The IRS isn't trying to trick you, they just want accurate reporting. You've got this! The fact that you're asking these questions now shows you're already ahead of where I was. 🙂