As someone who was in your exact shoes last year with my first Vanguard ETF investments, I completely understand the confusion about qualified vs non-qualified dividends! What helped me the most was learning that this split is actually determined by two main factors: how long Vanguard has held the underlying stocks in the ETF, and how long you've held your ETF shares. For dividends to qualify for the lower tax rates, both you and the fund need to meet specific IRS holding period requirements. The good news is that broad-market ETFs like VOO, VTI, and VFH typically have high percentages of qualified dividends (usually 80-95% in my experience) because they hold established companies that meet the requirements. The variation you see quarter to quarter is completely normal and reflects changes in the fund's holdings and market conditions. For your 2025 tax filing, Vanguard will send you a 1099-DIV form that breaks everything down clearly - qualified dividends go in Box 1b, and you'll calculate non-qualified dividends as the difference between Box 1a (total) and Box 1b. Most tax software handles this automatically once you enter the form. My advice: don't overthink the optimization right now. VOO and VTI are excellent foundational choices that are already quite tax-efficient. Focus on consistent investing and let your understanding of the tax nuances develop naturally. The complexity seems overwhelming at first, but it becomes much more manageable after you go through one complete tax season with actual forms in hand!

As someone who just started investing in ETFs this year, this entire discussion has been incredibly enlightening! I had the exact same confusion when I received my first dividend statements from my VOO and VTI holdings. What really helped me understand the qualified vs non-qualified split was realizing that it's essentially a pass-through of the tax characteristics from the underlying companies. When the ETF holds stocks like Apple or Microsoft that pay qualified dividends (and the fund has held them long enough), that flows through to you as qualified. But if there are any REITs, recent purchases, or other special situations in the fund's holdings, those portions come through as non-qualified. I've found that keeping a simple log of my dividend payments has been really valuable - just tracking the date, amount, and qualified percentage for each payment. It helps you see the patterns over time and makes tax season much less intimidating. For other newcomers who might be feeling overwhelmed by all this complexity: don't let it discourage you from investing in solid broad-market ETFs like VOO and VTI. These funds are already very tax-efficient, and the learning curve really does get easier with actual experience. Focus on consistent investing first, and the tax knowledge will build naturally as you go through your first few dividend cycles! The most important thing is that you're investing in diversified, low-cost index funds. The qualified dividend percentages are generally quite good (80-95% in most cases), and Vanguard handles all the complex IRS compliance for you.

I'm in the middle of my OIC process and the waiting is brutal!!! Submitted everything 5 months ago and still showing as "pending" whenever I check the status online. Does anyone know if calling actually speeds anything up?

I went through the OIC process last year and it was one of the most stressful but ultimately rewarding experiences dealing with the IRS. My situation was similar to yours - owed about $38,000 due to business failure and medical issues. A few key things I learned: First, be absolutely honest and thorough with your financial documentation. The IRS will verify everything, and any inconsistencies will delay or kill your application. Second, don't underestimate how long it takes - mine took 14 months from start to finish, with multiple requests for additional paperwork. I did use a tax professional for the initial application, which cost me $3,500, but it was worth it for the peace of mind. They helped me calculate a realistic offer amount ($11,200 for my $38,000 debt) and made sure all the forms were filled out correctly. One thing nobody tells you - during the application process, the IRS stops collection activities, which was a huge relief. No more threatening letters or calls. Just be prepared for the emotional rollercoaster of waiting months without updates. The acceptance letter arriving was one of the best days of my life. Don't give up hope - if your financial situation truly warrants it, the program can work. Just be patient and meticulous with your paperwork.

Does anyone use tax software that handles the 4137 form well? I'm struggling with this on FreeTaxUSA. It keeps giving me errors when I try to enter my allocated tips.

As someone who's been doing taxes for restaurant workers for years, I want to add a few important points that might help. First, make sure you're not double-reporting tips that were already included in your W-2 Box 1 wages - this is a common mistake that can lead to overpaying taxes. Second, keep detailed records going forward! A simple phone app or notebook where you track daily cash tips will save you so much stress next year. The IRS expects tip earners to maintain contemporaneous records. Finally, if your total unreported tips are less than $20 per month from any single employer, you don't need to include those on Form 4137. But if you're consistently earning tips, you'll likely be over that threshold. The form might seem intimidating, but once you understand it's just calculating the Social Security and Medicare taxes on unreported income, it becomes much clearer.

Dealt with this exact situation when I worked for a company based in New York but I worked remotely from Florida. My W-2 had the NY address but I never set foot in NY for work. The important thing is where you physically worked, not the address on the W-2. If your paystubs show state withholding for MD and VA, then those are the states you file in. Ignore the DE address completely. When you input your W-2 in TurboTax, there should be an option somewhere to indicate that you worked in a different state than what's listed on your W-2.

As someone who works in payroll administration, I can confirm what others have said - this is unfortunately very common. Many companies use their headquarters address on all W-2s regardless of where employees actually work, which creates confusion. The key thing to remember is that state tax obligations follow the "source rule" - you owe taxes where you earned the income, not where your employer is located. Since you physically worked in VA for part of the year and MD for part of the year, those are your filing states. A few practical tips for your situation: - When TurboTax asks about your work location, override what it assumes from the W-2 address - Make sure your state withholding amounts (Box 17) match what was actually taken from your paychecks - Keep copies of your paystubs as backup documentation in case either state questions your filing You're absolutely right to be careful about this - getting it wrong can result in penalties or having to file amendments later. But don't stress too much - the states deal with these employer address mismatches all the time and your situation is straightforward once you know the rules.

I went through this exact same situation last year and completely understand your stress! The 1099-K from PayPal is essentially just a transaction report - it's showing that $12,350 moved through their system, but it's not determining what's taxable income. Here's what really matters: your BetRivers win/loss statement. That's the document that shows your actual gambling activity for tax purposes. Since you had a net loss of $3,200, you're actually in a better position than you might think. The way it works is you report your gross winnings (from the BetRivers statement, not the PayPal amount) as gambling income. If you itemize deductions, you can then deduct losses up to the amount of your winnings. But if your standard deduction is higher than what you'd get from itemizing (including the gambling loss deduction), you're better off just taking the standard deduction. Keep all your documentation - the 1099-K, your BetRivers win/loss statement, and any transaction records. If the IRS ever questions why your reported income doesn't match the 1099-K amount, you'll have clear evidence that those PayPal transactions were deposits and withdrawals, not gambling winnings. Don't let the 1099-K amount scare you into thinking you owe taxes on $12,350. Focus on what your actual gambling results were according to BetRivers' records.

I'm dealing with a very similar situation right now! Got a 1099-K from PayPal showing about $9,800 in transactions for my BetMGM deposits throughout the year, but like you, I actually ended up with a net loss when looking at my actual gambling results. What's been helpful for me is understanding that the 1099-K is basically PayPal's way of covering their bases with the IRS - they're required to report payment processing over $600 now, but that doesn't mean everything on there is taxable income. It's just showing money that moved through their system. Your BetRivers win/loss statement is definitely the key document here. That shows your real gambling activity for tax purposes. Even though you had a net loss of $3,200, you'll still need to report any gross winnings as income (from the BetRivers statement, not the PayPal amount), and then you can potentially deduct losses up to that amount if you itemize. The most important thing is keeping good records of everything - your PayPal 1099-K, the BetRivers win/loss statement, and any transaction histories. That way if there's ever a question about why your reported income doesn't match the 1099-K amount, you can show exactly what those transactions were for. It's definitely stressful when you first see that big number on the 1099-K, but you're on the right track questioning whether it's all actually taxable income. Focus on your real gambling results, not the payment processing total.