Don't forget that if you owe more than $1,000 and didn't have proper withholding or make estimated payments throughout the year, you might face an "underpayment of estimated tax" penalty (Form 2210) regardless of when you file or pay the balance due.

This is exactly the situation I was in last year! Here's what I learned the hard way: while there's no interest benefit to paying early (since interest starts accruing after April 15th regardless), filing early gives you peace of mind and more options. What really helped me was getting on a payment plan as soon as possible. Even if you can't pay the full amount by April 15th, paying SOMETHING reduces the balance that penalties and interest accrue on. For example, if you owe $5,000 but can scrape together $2,000 by the deadline, you'll only pay penalties and interest on the remaining $3,000. Also, don't beat yourself up too much about the withholding mistakes - it happens to more people than you'd think, especially when income changes or life circumstances shift. The key is learning from it and adjusting for next year. I immediately updated my W-4 after dealing with my tax debt and started making quarterly estimated payments to avoid the same mess this year. One last tip: if you're really stressed about the numbers, consider using the IRS Online Payment Agreement tool. It shows you exactly what your monthly payments would be and the total interest/penalties you'd pay under different scenarios. Having that concrete information really helped calm my nerves.

For your eBay business selling vintage video games and collectibles, I'd recommend looking at 451120 - "Hobby, Toy, and Game Stores" since video games seem to be your primary focus. This code specifically covers retailers of video games and would be most accurate for your business. If you're selling a really mixed variety where no single category dominates, then 454110 - "Electronic Shopping and Mail-Order Houses" would be the safer general e-commerce option. The key is to track your sales by category for a month or two and see what makes up the majority of your revenue. That should guide your NAICS code selection. And don't worry too much - you can always update it as your business evolves! One tip: make sure you're keeping detailed records of your inventory costs and shipping expenses. These are often the biggest deductions for eBay sellers regardless of which NAICS code you choose.

Great question! I went through this exact same process last year when I started treating my eBay selling more seriously. For your situation selling vintage video games and collectibles, I'd definitely lean toward 451120 - "Hobby, Toy, and Game Stores" since video games seem to be your main focus. This code is specifically designed for businesses that sell games and hobby items, which sounds like a perfect fit. However, if your sales are really mixed across different categories without one clear winner, then 454110 - "Electronic Shopping and Mail-Order Houses" gives you more flexibility as a general e-commerce classification. One thing that helped me decide was looking at my sales data for the past few months and calculating what percentage came from each category. If 60%+ of your revenue is from video games, go with the hobby/game store code. If it's more evenly split, the general e-commerce code is safer. Also, don't stress too much about getting it "perfect" - the IRS cares more about accurate reporting of your income and expenses than having the absolutely perfect NAICS code. You can always adjust it next year if your business focus changes!

9 Hi all, small business landlord here. Please make sure you're sending those 1099s correctly! I've had tenants who either don't send them at all (which is a problem) OR who report the same payment across multiple years (even worse). As others have said, just report what you actually paid in the calendar year. And please double-check the mailing address - I get so many 1099s sent to old addresses even though I've updated my W-9 multiple times.

This is such a common issue for small business owners who had payment difficulties during tough times. I went through something similar when I had to catch up on several months of contractor payments after a slow period. The key thing to remember is that 1099 reporting follows the "cash method" - you report payments in the year you actually made them, regardless of when the work was performed or when the debt was originally incurred. So for your situation, all the rent payments you made in 2024 should be reported on your 2024 1099-MISC to your landlord, even if some of those payments were for rent that was originally due in 2023. Don't worry about the timing mismatch - this is exactly how the IRS expects it to be handled. Your landlord will report this as 2024 income on their tax return, which will match your 2024 1099 reporting. Just make sure you have good records showing the dates you actually made each payment, and you should be all set. The IRS is used to seeing these situations where businesses catch up on past-due obligations.

Has anyone else noticed that a lot of accountants seem confused about S corp basis calculations? I've had three different CPAs give me three different answers about how to handle distributions when we've had prior losses.

I'd definitely recommend getting a second opinion on this. Based on what you've described, it sounds like your tax preparer might be misunderstanding something about your situation. The key issue is tracking your basis correctly. Your basis in the S corp stock starts with your initial investment, gets reduced by your share of losses, gets reduced by distributions you receive, and gets increased by additional capital contributions or your share of income. If you made additional capital contributions during 2024 (like the $75K you mentioned in another comment), those should increase your basis and likely eliminate any capital gains treatment on your distributions. Make sure your tax preparer has accounted for all capital contributions, not just your original investment. Also, if you've made any loans to the S corp (even informal ones where you paid business expenses out of pocket), those create "debt basis" which can help absorb losses and avoid capital gains on distributions. I'd suggest asking your tax preparer to show you the specific basis calculation they're using. They should be able to walk through: starting basis + capital contributions + income - losses - distributions = ending basis. If that number goes negative, only the negative portion would be capital gains. Don't just accept their conclusion without understanding the math behind it - this is a common area where even experienced preparers make mistakes.

I work with a lot of clients who hold commodity ETFs, and there's a shortcut for handling these tiny expense transactions in tax software. In TurboTax: 1. Enter the info exactly as shown on your 1099-B 2. When asked for cost basis, enter the same amount as the proceeds ($0.28 in your case) 3. For "Sales expenses not included in proceeds" enter $0 4. For acquisition date, use your original purchase date This creates a $0 gain/loss transaction, which is the most accurate way to report these. Some tax experts argue you could technically calculate a tiny gain/loss based on your average cost basis, but the amount is so negligible it's not worth the effort.

Just to add another perspective on this - I've been dealing with SLV for several years now and the headache factor really depends on your tax software and how many other investments you have. If you're using basic tax software and SLV is your only "complicated" investment, it's manageable once you understand the pattern. But if you have multiple commodity ETFs, REITs with complex distributions, and other special situations, these micro-transactions can really add up to a lot of manual entry work. One thing I learned the hard way: keep good records of your original SLV purchase dates and amounts. When you have multiple purchases over time and these tiny expense allocations happening annually, it can get confusing to track which shares correspond to which original purchase for the acquisition date reporting. I now keep a simple spreadsheet just for tracking this. The silver lining (pun intended) is that once you've done it a few times, you'll be able to handle these transactions quickly each year. Just remember that the IRS gets copies of these 1099-B forms, so you definitely need to report them even though the amounts are tiny.