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Don't forget you can also deduct your losses up to the amount of your winnings if you itemize deductions instead of taking the standard deduction. So if you won $195 but lost $100 getting there, you'd only owe taxes on $95 of gambling income. Just make sure you have records of both the wins AND losses!
Thais Soares
ā¢But isn't itemizing only worth it if all your deductions add up to more than the standard deduction? That's like $13,000+ for a single person. Seems like you'd need a lot more than some gambling losses to make itemizing worthwhile.
That's absolutely right. Itemizing only makes sense if your total deductions (including gambling losses, mortgage interest, certain state taxes, charitable contributions, etc.) exceed the standard deduction amount. For 2025, the standard deduction is projected to be around $13,850 for single filers. So unless you have significant other deductions, tracking gambling losses probably won't provide a tax benefit if your gambling activity is minimal like the OP's situation.
Nalani Liu
For small amounts like $195, most casual bettors just don't report it. Is it technically required? Yes. Will anything happen if you don't? Almost certainly not. The betting site won't report it to the IRS without hitting those W-2G thresholds others mentioned.
Axel Bourke
ā¢I wouldn't recommend this approach. Even small unreported income can cause issues if you're ever audited for other reasons. Better to report everything and stay clean.
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About those 529 plans - while they don't give federal tax deductions, check if your state offers tax benefits! I live in NY and we get a state tax deduction up to $5K per year per beneficiary ($10K for married filing jointly). Made a huge difference on our state taxes.
Thais Soares
ā¢This! I'm in Virginia and we get a $4,000 deduction per account on our state taxes. Definitely check your specific state rules - some states like Indiana even offer tax credits instead of deductions which are even better.
Exactly right! State benefits vary hugely - Pennsylvania and Montana have unlimited deductions for contributions, while states like Colorado, New Mexico, and others offer deductions up to the annual gift tax exclusion amount. Some states require you to contribute to their specific 529 plan to get the benefit, while others (like Arizona and Kansas) give you the deduction regardless of which state's plan you use. I'd recommend calling your state tax department directly to confirm what's available. The tax savings might not be as big as federal deductions, but they definitely add up over time, especially if you're contributing for multiple children.
Nalani Liu
For your property purchase idea, I did something similar buying a rental property. But don't just think about the mortgage interest deduction - consider the overall return. If you buy a $130k property with 20% down, your mortgage interest might only be $5-6k the first year, saving you maybe $1,300 in taxes if you're in the 22% bracket. But you could potentially also depreciate the property (except for the land portion), deduct property taxes, maintenance, insurance, etc. Plus hopefully the property appreciates in value and generates rental income. That's where the real benefit comes from. Don't buy property JUST for tax benefits - it needs to make sense as an overall investment.
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Marcus Marsh
Does anyone know if we can file normally (earlier than November) if we want to? My house was barely affected (just some minor leaking) and I'm actually expecting a pretty big refund this year. I'm in Santa Barbara County which is covered by the extension, but I'd rather get my refund sooner if possible.
Yes, you can absolutely file earlier! The November date is just the deadline - you can file anytime before then. If you're getting a refund, it definitely makes sense to file as soon as you're ready.
Cedric Chung
One important thing that hasn't been mentioned yet - if you make estimated tax payments, this extension also applies to those. So the Q1 and Q2 2025 estimated payments that would normally be due April 15 and June 15 are now also extended to November 16. This was a huge relief for me since my small business got hit hard by the flooding and cash flow has been a nightmare. Being able to delay those estimated payments while we rebuild is actually making a significant difference.
Talia Klein
ā¢Does anyone know if we'll get hit with an underpayment penalty if we don't make any estimated payments until November? Usually you're supposed to pay quarterly but this situation seems different.
Cedric Chung
ā¢Based on what I learned from the IRS when I called, you won't face underpayment penalties for delaying these specific estimated payments until November 16th. The disaster relief specifically waives penalties for these delayed payments. However, it's important to note that this only applies to the specific payment deadlines that fall within the relief period. Future estimated payments beyond this period would still follow the regular schedule and penalty rules.
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One thing nobody mentioned yet - make sure you're keeping good records of all your investment purchases and sales! The IRS requires you to track your "cost basis" (what you paid for the investment) to calculate your gains or losses accurately. Most brokerages now report this information to the IRS on Form 1099-B, but sometimes the information is incomplete or incorrect. I learned this the hard way when I couldn't prove my original purchase price for some stocks I'd held for years.
Do you have any tips for how to keep track of all this? I've been investing through multiple platforms (Robinhood, Vanguard, and a little crypto on Coinbase) and I'm worried about keeping everything straight for next year's taxes.
I recommend downloading annual tax documents from each platform and saving them in a dedicated tax folder on your computer. Name each file with the year and platform (like "2025_Robinhood_1099.pdf"). For crypto especially, consider using a dedicated tracking app that can integrate with multiple exchanges to create a comprehensive tax report. Some platforms like CoinTracker or Koinly can sync with Coinbase and other exchanges to track your cost basis automatically. The few minutes spent organizing throughout the year will save you hours of stress during tax season.
Justin Trejo
Quick tip: If you're married filing jointly, the capital loss deduction limit is still $3,000 total (not $3,000 per person). My spouse and I found this out when we tried to deduct $6,000 in losses and got our return rejected.
Alana Willis
ā¢Are you sure about that? My accountant let us deduct $3,000 each last year. Maybe the rules changed for the 2025 filing season?
Sean Kelly
One thing nobody's mentioned yet - if your income fluctuates a lot throughout the year (which is common for freelancers), you might want to look into the "annualized income installment method" instead of just dividing your expected tax by four. Basically, you can pay estimated taxes based on what you've actually earned so far each quarter, rather than paying equal amounts. It's a bit more complicated to calculate, but it's helpful if your income isn't consistent and you don't want to overpay early in the year. Form 2210 Schedule AI is what you'd use when filing. It's a bit more work but can really help with cash flow if your income is seasonal or unpredictable.
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Isabella Costa
ā¢This is super helpful - my income definitely fluctuates! How complicated is the calculation? Is there a simple formula I could use or do I need special software? I'm trying to avoid paying for a tax professional if possible.
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Sean Kelly
ā¢The calculation isn't super simple, but it's doable without professional help. You basically track your income, deductions, and credits for each payment period, then calculate the tax on that amount as if it were your annual income (annualizing it). There's no single formula since it depends on your particular tax situation, but the IRS has worksheets in Publication 505 that walk you through it step by step. Most tax software can help with this too if you input your quarterly income data. I'd recommend at least trying the calculation once to see if it's manageable for you. The benefit is that if you earn most of your income later in the year, you won't have to make large estimated payments before you've actually earned the money.
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Zara Mirza
Don't overlook state estimated taxes too! Everyone's talking about federal, but depending on your state, you might need to make state quarterly payments as well. Some states have different thresholds and due dates. For example, I'm in California and got hit with a penalty because I made federal quarterly payments but completely forgot about state ones my first year freelancing.
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Luca Russo
ā¢Good point! I'm in Texas so I lucked out with no state income tax, but my friend in New York had the same issue as you. Do most states use the same payment deadlines as the federal ones?
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