This is such a helpful thread! I'm dealing with a similar situation where my uncle gifted me some Apple stock he'd held for about 8 years. From what I'm reading here, it sounds like I'd qualify for long-term capital gains treatment even if I sell immediately, which is a huge relief since short-term rates would be brutal. One thing I wanted to add that might help others - if you're missing the original purchase documentation, some brokerages will actually provide a "gift basis statement" that shows the cost basis information when stocks are transferred as a gift. I got one from Schwab and it had all the details I needed including the original purchase date and price. Definitely worth asking your brokerage about this specific document if you're having trouble tracking down the information from the original owner. Also, make sure to keep any gift documentation (like transfer confirmations) for your records since the IRS may want to see proof that these were actually gifted shares and not purchased by you directly.

Great thread everyone! I'm a tax professional and wanted to clarify a few key points that might help others in similar situations: 1. **Holding Period**: As Mohammad correctly mentioned, you inherit the donor's holding period. If your grandmother held the stocks for more than a year, you get long-term treatment regardless of how long you've owned them. 2. **Cost Basis**: You generally take the donor's original cost basis (carryover basis), NOT the fair market value when you received the gift. This is different from inherited assets where you get a "stepped-up basis." 3. **Documentation**: The most important documents you need are: - Proof of the gift transfer (brokerage statements) - Original purchase information (date and price the donor paid) - Fair market value on the gift date (important for certain loss calculations) 4. **Special Loss Rule**: If the stock's value when gifted was LESS than what the donor originally paid, there are special dual-basis rules for calculating losses that can get complicated. One thing I'd add to the great suggestions here - if you're still missing documentation, the IRS allows reasonable estimates based on historical stock prices for the relevant dates, as long as you can document your methodology. But always try to get the actual records first through the methods others have mentioned (brokerages, IRS records, etc.).

Another important consideration is that the IRS has actually delayed full enforcement of the $600 1099-K threshold. For 2023 and 2024 tax years, they're using a higher threshold of $5,000 while they work out implementation issues. However, payment processors like Venmo might still issue 1099-K forms at the lower threshold, so you could still receive one even if the IRS isn't fully enforcing it yet. That said, the advice about keeping good records and being able to document that your fantasy league is a personal hobby activity remains crucial. If you do get a 1099-K, don't panic - just make sure you can show this isn't business income. Keep your league charter, entry fee records, and any communication showing this is just friends playing fantasy football together. One more tip: consider rotating who collects and distributes the money each year among different league members. This spreads out the 1099-K risk and prevents one person from consistently appearing to receive large payments that might look like business activity to automated systems.

One thing worth mentioning is that you should also consider how you categorize the payments within Venmo itself. When sending money, Venmo asks whether it's for "goods and services" or if it's personal. Always select the personal option for fantasy football payments, and avoid using business-related descriptions. Also, keep in mind that even if you do everything right to minimize 1099-K issues, you should still maintain good records of your league. Document the recreational nature - things like league rules, roster of participants, entry fees paid by everyone, and evidence that this is just friends having fun rather than any kind of profit-seeking venture. If you're really concerned about the reporting threshold, you might want to consider hybrid payment methods. For example, collect entry fees digitally but distribute winnings through multiple smaller payments spread over time, or mix digital payments with cash for the final payouts. This can help keep individual payment amounts below levels that might trigger automatic business income assumptions.

Has anyone mentioned quarterly estimated taxes yet? If ur making ANY profit with ur LLC, ur supposed to be paying taxes quarterly, not just at year end. I learned this the hard way and got hit with penalties my first year!!

Just wanted to add something that might help with the quarterly tax situation - if your business had a loss last year (like yours did), you don't need to make quarterly payments for that year. But if you expect to be profitable in 2024, you'll want to start making estimated payments. The safe harbor rule is helpful too - if you pay at least 100% of what you owed last year (110% if your prior year AGI was over $150k), you won't get penalties even if you end up owing more. Since you had no business profit in 2023, your safe harbor amount would just be based on any other income you and your spouse had. Also, don't stress too much about the amendment process. I amended my return last year to add my LLC income and it was pretty straightforward through TurboTax. The key is just making sure you have all your business expenses properly categorized. Keep digital copies of everything - receipts, bank statements, platform fees from Etsy, etc. The IRS is actually pretty reasonable when you're clearly trying to comply and report everything correctly.

5 My dad started taking social security at 67 while still working part time as a consultant. His big mistake was not realizing how it would affect his tax bracket! He ended up in a higher bracket and actually netted less overall than if he'd waited till 70 when he fully retired. Sometimes the extra SS income can actually hurt you financially if you're not careful.

One thing I'd add to this great discussion - don't forget to consider the "do-over" rule if you change your mind. If you start collecting Social Security and later decide it wasn't the right choice, you have 12 months from your first benefit payment to withdraw your application and pay back everything you received (without interest). This essentially gives you a one-time reset. Also, if you're married, coordinate your claiming strategy with your spouse! The timing of when each spouse claims can significantly impact survivor benefits. Sometimes it makes sense for the higher earner to delay while the lower earner claims early, or vice versa. Given that you're an accountant, you probably already know this, but make sure you're factoring in the time value of money when comparing scenarios. A dollar today is worth more than a dollar in three years, so even though delaying increases your monthly benefit, the total lifetime value calculation can be tricky depending on your investment returns and life expectancy assumptions.

I went through this exact same confusion last year! The 898 code really threw me for a loop too. What everyone else has explained is spot on - that $0.00 amount next to "Refund applied to non-IRS debt" is actually great news. It means the IRS automatically checked if your partner owed any money that could be taken from his refund (like unpaid child support, defaulted student loans, back taxes to states, etc.) through their Treasury Offset Program, but they found nothing to collect. So he definitely got his full $1,055 refund! The math works out perfectly: $1,819 withholding minus $764 tax liability equals $1,055. That February 26th date next to code 846 shows when the money was actually sent to his bank account. Those weird future dates like March 2026 are just the IRS using their ancient computer system's processing cycles - they don't mean anything actually happened in the future. I remember staring at similar dates on my transcript thinking I was looking at some kind of time-travel tax return! 😅 Your partner's transcript looks completely normal and healthy. No red flags at all!

I just wanted to thank everyone who responded to my question! This thread has been incredibly helpful and educational. When I first saw that 898 code on my partner's transcript, I was so worried something was wrong or that money was being taken from his refund for some unknown debt. But thanks to all your explanations, I now understand that: - The 898 code with $0.00 is actually GOOD news - it shows the IRS checked for any debts through the Treasury Offset Program and found none - He got his full $1,055 refund ($1,819 withholding - $764 tax liability = $1,055) - Those weird March 2026 dates are just internal IRS processing cycles, not actual calendar dates - The February 26th date next to code 846 is when the refund was actually sent I had no idea the IRS automatically checks every refund for potential debt offsets - that's actually pretty smart of them, even if their transcript format is confusing as heck! You all have made me feel so much more confident about understanding these documents in the future. The IRS should definitely hire some of you to make their explanations more user-friendly! 😊 Thanks again everyone - this community is amazing! 🙏