Probably unpopular opinion but... just take the money and pay the taxes? All these complicated schemes to save on taxes often end up costing more in professional fees and stress than they save. Plus some can put you in audit territory. My brother won about $200k and just paid the taxes. Simple. No stress. No worrying about IRS problems. And honestly, you still have hundreds of thousands left after taxes. Not worth the headache trying to squeeze out every last dollar imo.

Congratulations on your win! As someone who works in tax preparation, I'd strongly recommend getting professional help given the size of this windfall. One important consideration nobody's mentioned yet - timing your claim strategically. If you're close to year-end, you might want to think about whether to claim in 2025 vs early 2026, depending on your other income and potential tax law changes. Also, make sure you understand California's specific lottery tax rules. CA doesn't tax lottery winnings at the state level the same way as regular income - there are some nuances that could affect your planning. The charitable contribution strategy mentioned earlier is solid, but remember the 60% AGI limitation means you can't offset the entire win in one year through donations alone. You might need to spread charitable giving across multiple years to maximize the tax benefit. Whatever you decide, don't rush into anything. The lottery commission usually gives you several months to claim, so use that time to get proper advice and make informed decisions. This is definitely a situation where spending a few thousand on quality professional guidance could save you tens of thousands in taxes.

Don't forget that property tax rules can vary by state! In some places, property taxes are paid partly in advance rather than fully in arrears. And some counties have weird fiscal years that don't align with calendar years. Might be worth a quick call to your county tax assessor's office to confirm exactly how your local system works before making any decisions.

Great question! I went through the exact same confusion when I bought my first home. The key thing to remember is that for individual taxpayers, property tax deductions follow the "cash basis" rule - you can only deduct what you actually paid out of pocket to the tax authority in that tax year. Since your escrow account didn't make any property tax payments in 2023, you won't have a property tax deduction for your 2023 return. The credit you received at closing from the seller is considered a purchase price adjustment, not a tax payment by you. When you pay the 2023 property taxes in January 2024 (even though they're for the previous year), that's when you'll get the deduction - on your 2024 tax return that you'll file in 2025. Make sure to keep your closing statement and all escrow records organized, as you'll need them for future reference and when you eventually sell the home.

Has anyone had their employer's matching funds audited? My company matches 2-to-1 on Giving Tuesday too, but I've always wondered if I should be including the company match in my charitable deduction or just my original donation amount.

I went through this exact same situation last year with my Giving Tuesday donations! The key thing to remember is that you claim charitable deductions based on when YOU made the donation, not when the charity received the funds or issued the receipt. Since you made your donations on December 3rd through Benevity, those donations belong on your 2024 tax return, even though the charity didn't receive the money until January 2025. The IRS considers the donation "complete" when you authorize the payment through the platform. I'd recommend keeping records of both your Benevity confirmation (showing the December date) and the charity receipt (showing the January date) in case you ever need to explain the timing discrepancy. The Benevity platform should have given you a confirmation or receipt showing the December 3rd date - that's your primary documentation for tax purposes. You've been handling this correctly all along by claiming donations based on when you made them rather than when the organizations received them!

Great question about donation limits! For individual taxpayers, charitable contributions are generally limited to 60% of your adjusted gross income (AGI) for cash donations to public charities like schools. Any excess can be carried forward for up to 5 years. For businesses, the rules are different depending on your entity type. Since you mentioned you're an LLC taxed as an S-Corp, any business charitable contributions would actually flow through to your personal return anyway, so you'd still be subject to the individual limits. However, if you can legitimately structure part of it as advertising expense (like Zara suggested), that wouldn't count against your charitable contribution limits at all. The key is making sure whatever you do is properly documented and has a legitimate business purpose. Given the complexity and potential audit risk when your child attends the school, I'd really recommend waiting for your accountant to return before making any decisions. The IRS scrutinizes these situations closely.

I've been through this exact scenario with my consulting business and my daughter's private school. Here's what I learned after working with both my CPA and a tax attorney: The IRS has a doctrine called "private benefit" that applies here. Even if the school is a legitimate 501(c)(3), if your donation provides a substantial private benefit to you or your family, it's not fully deductible. This includes indirect benefits like your child receiving better facilities or programs. However, I found a middle-ground approach that worked well. I split my contribution: 1. A portion went toward legitimate business advertising (program ads, event sponsorship with clear promotional value) 2. The remainder was a personal charitable donation on my individual return For the advertising portion, I made sure to get proper invoices detailing the marketing services provided, and I kept all materials showing my business was actually promoted. This part was fully deductible as a business expense. The key is documentation and reasonable business justification. If you can't articulate a legitimate business reason for the expense beyond helping your child's school, the IRS will likely view it as a personal donation disguised as a business expense. I'd strongly recommend waiting for your accountant to return before proceeding. The audit risk on these transactions is higher when there's a family connection, so you want to make sure everything is bulletproof from a documentation standpoint.

Lol your boss is stuck in 2017! Mine said the same thing and I almost filed wrong because of it. The tax prep software kept asking about "unreimbursed employee expenses" and I entered everything but then got confused when it didn't seem to do anything with that info. Called my cousin who's an accountant and she explained the 2018 changes. Apparently the only real solution is to get your employer to reimburse you directly. My company now has a much better expense policy because so many employees complained after realizing they couldn't deduct stuff anymore.

Your supervisor means well, but they're definitely giving you outdated advice from before the Tax Cuts and Jobs Act. As others have mentioned, W-2 employees lost the ability to deduct unreimbursed business expenses in 2018. However, I'd suggest having a conversation with your company about their expense reimbursement policy. Since you're traveling regularly and they're already covering mileage and per diem, they might be willing to expand coverage to include things like safety equipment and protective gear that are genuinely necessary for your job duties. Many employers don't realize how the 2018 tax changes shifted the burden back to companies. What used to be a shared cost (employee pays upfront, gets partial tax benefit) is now entirely on the employee unless the company reimburses. It's worth framing it that way when you approach them - you're not asking for extras, you're asking them to cover legitimate business expenses that employees can no longer write off. Keep those receipts anyway though - you never know if the rules will change again, plus some states still allow these deductions even when federal doesn't.