Congratulations on the big win! You're absolutely right to report this properly. Here's what you need to do: Report the $24,000 net gambling profit as "Other Income" on Schedule 1 (Form 1040), line 8b. Write "Gambling winnings" in the description. The fact that DraftKings didn't issue a W-2G doesn't matter - you're still legally required to report all gambling income. For your losses, you can deduct them on Schedule A up to the amount of your winnings, but this means you'll need to itemize instead of taking the standard deduction. Run the numbers to see if itemizing makes sense for your situation. Documentation is crucial since you don't have official tax forms. Keep screenshots of your DraftKings account history, bank statements showing deposits/withdrawals, and create a detailed gambling log with dates, amounts, and outcomes for each session. The IRS does audit gambling income, especially large amounts without corresponding tax forms. One important point: even without sending you a W-2G, DraftKings likely reports high-volume accounts to the IRS through other compliance mechanisms. With $29k in winnings, your account activity probably triggered internal reporting requirements, so the IRS may already have some record of your gambling activity. Better to report everything accurately than risk penalties later.

Just wanted to chime in as someone who went through a similar situation last year. You're definitely doing the right thing by reporting this - I made the mistake of initially thinking I could "wait and see" if the IRS noticed, but after doing more research I realized that was a terrible idea. One thing I learned that might help you: even though you didn't get a W-2G from DraftKings, they likely have detailed records of your account activity that could be shared with the IRS if requested. Online gambling platforms are subject to various reporting requirements, especially for accounts with significant activity like yours. I'd also recommend keeping a spreadsheet or log of all your gambling activities going forward - dates, sites, amounts wagered, wins/losses, etc. It makes tax time so much easier and gives you solid documentation if you ever face questions from the IRS. For this year's filing, definitely report the full $24k net profit on Schedule 1. Whether itemizing to deduct your losses makes sense depends on your other deductions, but at least you'll have reported the income correctly. Good luck with everything!

Don't forget about foreign stocks if your dad had any! My mother inherited some Canadian company stocks from my father, and there were special rules about foreign securities that almost caused us to miss out on significant tax advantages. The step-up basis applies, but there can be currency conversion considerations too. The broker should be handling this, but it's worth specifically asking how they're determining the stepped-up basis for any foreign investments. In our case, they initially only adjusted for the stock price change but missed the currency fluctuation component.

I'm sorry for your loss, Aisha. Going through this process while grieving is incredibly difficult, and I can relate to feeling overwhelmed by all the financial details. One thing I haven't seen mentioned yet is the importance of getting multiple copies of the death certificate from the funeral home or vital records office. Each brokerage will likely want an original or certified copy, and if your father had accounts at several firms, you'll need quite a few. I learned this the hard way when we had to wait weeks for additional copies while the estate settlement was delayed. Also, keep detailed records of everything - dates you contacted each brokerage, names of representatives you spoke with, and any reference numbers they give you. Some brokerages are much faster at processing these requests than others, and having good documentation helps if you need to follow up or if there are any discrepancies later. The step-up basis will definitely help reduce future tax burdens when your mom eventually sells any of these investments, so it's worth taking the time to get it done properly. Wishing you and your family the best as you navigate this difficult time.

I'm so sorry you're going through this stress, especially with medical bills adding to the pressure! 😰 As someone who went through almost this exact scenario earlier this year, I can tell you that your timeline is actually very normal for amended returns. The 846 code with 11/5 date plus WMAR showing "adjusted" is exactly what you want to see - it means your refund was fully approved and the check should have been mailed right around that date. Since today is around 11/10, you're still well within the typical 5-7 business day USPS delivery window. I know the waiting is absolutely brutal when you need the money urgently, but amended returns are always sent as paper checks regardless of your direct deposit info. If you haven't already, definitely set up USPS Informed Delivery - it'll show you a preview of incoming mail each morning which really helps with the mailbox-checking anxiety. Also watch out for a very plain white Treasury envelope that honestly looks like junk mail - I almost threw mine away! Try to hang in there until around 11/15 before escalating. Your money is definitely coming - just at government speed! 🤞

I totally feel for you - that waiting period after seeing the 846 code is so stressful, especially when you have medical bills piling up! 😔 From everything shared here, it really sounds like you're tracking normally for an amended return. The combination of your 846 code dated 11/5 and WMAR finally showing "adjusted" is actually great news - it means all the processing hurdles are cleared and your check was likely mailed right around that date. Since today is around 11/10, you're still in that typical 5-7 business day USPS delivery window everyone mentioned. I know it's torture waiting when you desperately need the money, but amended returns pretty much always come as paper checks regardless of your banking info. Definitely sign up for USPS Informed Delivery if you haven't - it'll at least give you a morning preview of what's coming so you're not anxiously checking the mailbox all day. And watch for a super plain white Treasury envelope that honestly looks like it could be junk mail! Try to hang in there until around 11/15 before panicking. Your refund is definitely approved and on its way - just moving at typical government speed! 🤞

Has anyone used an umbrella LLC with a separate tax election for the entity? My CPA suggested forming an LLC but then electing to have it taxed as an S-Corporation (Form 8832 followed by Form 2553). He said it gives the liability protection and flexibility of an LLC with the tax benefits of an S-Corp.

This is a great discussion thread! I'm in a very similar situation - household income around $380K and considering a side business. One angle I haven't seen mentioned much is the state-level implications. I'm in Texas (no state income tax), but for those in high-tax states like California or New York, the state treatment of S-Corps vs LLCs can significantly impact the overall analysis. Some states don't recognize S-Corp elections and will tax the entity at the corporate level regardless. Also, regarding the ownership question - even if your spouse isn't actively involved, there could be estate planning benefits to joint ownership, especially if the business becomes successful. If something happens to you, having your spouse as a co-owner can simplify business continuity compared to having to transfer a sole proprietorship through probate. Has anyone factored in the potential exit strategy implications? If you plan to eventually sell the business or bring in outside investors, the corporate structure (even if taxed as S-Corp) might be more attractive to buyers than an LLC structure.

I'm dealing with a similar situation but have a twist - I work part-time at a hospital (W-2) and also do some telehealth consulting work as an independent contractor (1099). From what I'm understanding in this thread, I can't deduct scrubs for my hospital job, but could potentially deduct them for my consulting work if I need to wear them during video calls with patients? Also wanted to mention that some hospitals have started offering "scrub allowances" as part of their benefits package instead of reimbursement programs. It's basically a small monthly stipend (like $25-50) that goes toward uniform costs. Might be worth asking HR if they're considering something like that, especially if you can get other new hires to ask too. Our hospital implemented this after several departments complained about the uniform costs. One last thing - if you're union, definitely bring this up with your union rep. Ours has been pushing for better uniform benefits since the tax deduction went away, and they've had some success getting management to increase reimbursement percentages.

Thanks for all the detailed responses everyone! As someone who handles tax preparation professionally, I wanted to add a few clarifying points that might help: First, @Liam McConnell - the FSA route that @Ava Martinez mentioned is probably your best current option as a W-2 employee. You can set aside pre-tax dollars during open enrollment and use them for required work uniforms. Just make sure you estimate conservatively since FSA funds are "use it or lose it" in most cases. Second, regarding state deductions - it's worth checking your specific state even if it generally conformed to federal changes. Some states have carve-outs or different rules for healthcare workers specifically. A quick call to your state's tax department or checking their website can save you from missing potential deductions. Finally, I'd recommend documenting everything about your scrub requirements - emails from HR, employee handbook excerpts, etc. If the federal deduction does return after 2025 as @Joshua Hellan mentioned, having this documentation will be crucial for substantiating that these were truly required uniforms and not regular clothing. The landscape is definitely frustrating for healthcare workers right now, but there are still some workarounds if you plan strategically!