Great question! I went through this exact confusion when I had some casino winnings last year. The key thing to understand is that gambling winnings are treated as ordinary income, which means they get added to all your other income and taxed at your marginal tax rate - not a flat 24%. The 24% you're seeing is just the federal withholding rate that casinos are required to take out on certain large winnings (like jackpots over $5,000). Think of it like the taxes withheld from your paycheck - it's just an advance payment toward what you'll actually owe. So for your $800,000 example, here's what would happen: 1. Casino withholds 24% federal ($192,000) plus any state taxes 2. At tax time, you add the full $800,000 to your other income 3. If this pushes you into the 37% bracket, you'd owe 37% on the portion in that bracket 4. You'd either get a refund if they over-withheld, or owe more if they under-withheld Also don't forget - you can deduct gambling losses up to your winnings if you itemize and keep good records. Save those losing tickets and keep a gambling diary! The most important thing is to set aside extra money beyond what they withhold, because you'll likely owe more at tax time.

Just to add another perspective - I work as a tax preparer and see gambling tax situations all the time. One thing that trips people up is that the withholding rates can vary depending on what you win and where you win it. For example, if you win at a tribal casino, they might not withhold anything at all even on large jackpots, because they follow different rules. But you still owe the same taxes! I've had clients who thought they were "tax-free" wins and then got shocked at filing time. Also, if you're a regular gambler, keep in mind that the IRS can sometimes classify you as a "professional gambler" if you gamble frequently enough, which changes how you report everything. It's rare, but worth knowing about if you spend a lot of time at casinos or playing online. The safest approach is always to assume you'll owe taxes at your marginal rate and set aside that percentage of any winnings, even if nothing was withheld. Better to have extra money saved than to scramble come tax time!

i know everyone hates wmr but maybe just use that for now? better than nothing

I'm dealing with the exact same issue! Filed on 1/28 and getting that same "We are not able to provide assistance to you via the identity verification tool" message. It's so annoying because I've been checking my transcripts for the past 3 years without any problems. The system worked fine when I checked it in December for prior year info, but now suddenly it won't verify my identity? Makes no sense. I even tried using different browsers and clearing my cache but nothing works. Really hoping this gets fixed soon because WMR is practically useless compared to the detailed info you get from transcripts.

I'm confused by all of this tbh. Last year I got a $120 settlement check with no 1099 at all, and the year before I got one with a 1099 that had nothing written on it about taxes. Why is there no consistency??

The inconsistency you're seeing is actually pretty normal with class action settlements. Each settlement administrator and their legal counsel make independent decisions about tax reporting based on the specific nature of that settlement. Some factors that affect whether you get a 1099: - Settlement amount (many don't issue 1099s under $600) - Type of damages being compensated - How cautious the administrator wants to be - Whether the settlement clearly falls into taxable vs non-taxable categories Your $120 settlement without a 1099 was probably either under their reporting threshold or clearly determined to be non-taxable from the start. The one with the blank 1099 sounds like they were being extra cautious but didn't have specific tax guidance to include. Bottom line: if you don't get a 1099, you generally don't need to report it. If you do get one with a note saying it's not taxable, keep the documentation and follow their guidance. The settlement administrators usually have tax attorneys making these determinations, so their guidance is typically reliable.

I was charged $580 last year for something similar, but my situation included rental property, multiple state filings, and cryptocurrency transactions. For just a Schedule C with a few 1099s, that's much steeper than what I'd expect compared to other tax scenarios I've encountered. My sister-in-law has a nearly identical tax situation to yours and pays around $350 in the Midwest. Even accounting for potential regional differences, $626 seems about $200 too high unless there are complicating factors you haven't mentioned.

I'd definitely get a second opinion on that pricing. I'm an EA and typically charge $385-425 for a 1040 with Schedule C and multiple 1099-NECs, depending on complexity. The $626 quote seems high unless there are additional factors like depreciation calculations, complex inventory accounting, or multi-state issues. A few questions that might affect pricing: Do you have significant business asset purchases requiring depreciation? Any employee-related forms like 941s? Home office deduction calculations? These can add time and complexity. But for straightforward freelance/contractor income with basic business expenses, you should be looking at $350-450 range max. I'd recommend calling 2-3 other preparers for quotes - most will give you a ballpark over the phone once you describe your situation.

Anybody know if this same rule applies to other rental expenses too? Like if I buy cleaning supplies that I use at both properties, do I need to split that cost too?

Great question! I actually had a similar situation last year with two rental units in the same building complex. After consulting with my CPA, I learned that the correct approach is definitely to split the mileage proportionally - not claim the full amount for each property. Here's what I do now: I keep a simple spreadsheet where I log each trip with the total miles, then note what percentage of time/work was spent at each property. For your example, if you spent equal time at both units, you'd allocate 7 miles to each property on their respective Schedule E forms. The IRS views this as one business trip that served multiple properties, so the expense should be divided accordingly. Claiming 14 miles on both would indeed be double-dipping and could raise red flags during an audit. I've found that being conservative and well-documented with these allocations has saved me headaches down the road. One tip: I also photograph my odometer readings and keep brief notes about what work I did at each property. Makes tax time much smoother!