How exactly does this work? Do you just transfer shares directly to the charity somehow? And do all charities accept stock donations or just the bigger ones?

You transfer the shares directly to the charity's brokerage account - most medium and large charities have a process for this. You'll need to contact their donation department for their specific instructions. They'll usually provide their broker info and account number. Many smaller charities can accept stock donations too, but some might not have the infrastructure. In those cases, there are donor-advised funds like at Fidelity or Schwab where you can donate the stock to the fund (getting the tax deduction immediately), then grant the money to any charity from there. The best part is you completely avoid the capital gains tax you would've paid if you sold the stock yourself, plus you still get the full market value as a deduction.

Technically those are deductible but practically not worth the hassle. You'd need receipts for everything, and most stores don't automatically provide them for these small donations. Plus, if you're taking the standard deduction anyway, they won't help your tax situation at all.

Thank you for mentioning this! Do you know if they help with tip income situations specifically? That's the part my cousin is most worried about.

Yes, they absolutely help with tip income situations! In fact, that's one of the most common issues they deal with for restaurant workers. They can help your cousin figure out how to reconstruct reasonable tip records if they didn't keep detailed logs, and they understand the specific challenges facing tipped employees. The LITC volunteers typically include tax professionals who donate their time and have experience with these exact scenarios. They won't judge your cousin for not filing - their goal is just to help people get into compliance with the least financial pain possible.

How far back can you claim refunds? My boyfriend hasn't filed in like 6 years but he's pretty sure he'd get refunds.

You can only claim refunds going back 3 years. So for the 2025 filing season, you can claim refunds for 2022, 2023, and 2024. Any potential refunds from years before that are unfortunately lost forever - that's why it's important to file ASAP if your boyfriend thinks he's due refunds! For the older years (beyond the 3-year window), he should still file the returns to get into compliance, but he won't be able to get any refunds from those years even if the calculations show he would have been entitled to them.

Is there any downside to having an IP PIN? Like does it delay refunds or make your return more likely to be audited? I'm wondering if i should request one proactively.

There's no direct connection between having an IP PIN and being audited more frequently. The main downside is the extra step required each year and the potential complications if you forget to use it or lose it. As for refund delays, having an IP PIN shouldn't cause delays if you use it correctly. However, if you file without it or use an incorrect PIN, then yes, you'll face significant delays since you'll need to paper file and include an explanation. For most people who haven't experienced identity theft, I don't recommend proactively requesting one unless you have specific security concerns. It adds a permanent extra step to your annual tax filing that can't easily be undone.

H&R Block definitely does NOT save the IP PIN between years. I learned this the hard way. For security reasons, you need to manually enter a new IP PIN each year. The IRS issues a completely new PIN annually, and no tax software is allowed to store it from previous years.

Thanks for bringing up special allocations - I wasn't familiar with that concept or the "substantial economic effect" requirement. What exactly counts as having "economic effect beyond tax savings"? Would things like my wife handling all the management responsibilities as GP while I provide most of the funding as LP qualify? And yes, we've considered an S-Corp too, but I was concerned about the "reasonable salary" requirement. Our business is projected to make around $300k/year, and I wasn't sure what would be considered "reasonable" for our industry (real estate investments).

Your wife handling all management responsibilities while you provide funding could potentially create economic effect beyond tax savings, as it reflects the different roles you're playing in the business. Document her actual time spent, decisions made, and management activities to substantiate her role. The key is having her GP role reflect genuine business operations, not just a paper arrangement. For S-Corps in real estate investing with $300k annual income, reasonable salary benchmarks typically range from $60k-$120k depending on location, portfolio size, and actual services performed. The IRS looks at comparable compensation for similar roles in your market. I recommend researching salary surveys for real estate investment managers in your area to establish a defensible figure.

The IRS calculator is pretty basic and doesn't account for complex allocations. I'd recommend the tools at business.gov instead - they're more comprehensive. And yes, states definitely have different rules! California is particularly strict with partnership structures and charges an $800 minimum annual tax regardless of profitability. New York and Delaware have more favorable treatments. Check your state's secretary of state website for specific requirements.

Thanks for the business.gov suggestion! I'll check that out instead. And I had no idea California charges $800 annually regardless of profit - that's good to know since we might expand there eventually. I'll definitely look up my state's requirements on the secretary of state website.

I think you're right. I got a big promotion last year and our withholding never got adjusted. Is there a specific amount I should put for additional withholding on the W-4? And will I get penalized for having paid so little throughout the year?

You should use the IRS Tax Withholding Estimator on their website to calculate the exact amount for additional withholding. With your income level, you might consider putting an additional $500-700 per paycheck depending on your pay frequency. You might face an underpayment penalty if you didn't pay at least 90% of your tax liability during the year or 100% of last year's tax (110% if your income was over $150,000). The penalty isn't usually huge, but it's better to avoid it by making an estimated tax payment now if you can. You can make an estimated payment for 2025 using Form 1040-ES to help reduce any potential penalties.

I used H&R Block online and it was pretty straightforward. There's a specific section for unemployment compensation where you enter the 1099-G info. Make sure you're looking at box 1 on the form for the total unemployment amount and box 4 for any federal withholding.