Just want to make sure the OP and others understand capital gains taxes for 2025 filing. If you hold your investments for more than a year before selling (long-term capital gains), you get a much better tax rate (0%, 15%, or 20% depending on your income) than short-term gains (taxed as ordinary income). Making this distinction could literally save you thousands on your tax bill! I learned this the hard way when I day-traded some stocks and got hit with ordinary income rates on everything.

Great advice from everyone here! Just want to add one more consideration for @Ava Kim - since you're working at Target and trading stocks, you might want to look into tax-loss harvesting if you have any losing positions. You can sell losing stocks to offset your capital gains, which reduces your overall tax liability. For example, if you made $30k in gains but also have $10k in unrealized losses, you could sell those losing positions to bring your taxable gains down to $20k. You can even carry forward losses beyond your gains (up to $3k per year against ordinary income). This strategy works best when combined with the estimated payment approaches others mentioned. Just make sure to avoid the wash sale rule - don't buy back the same or "substantially identical" securities within 30 days of selling for a loss, or the IRS will disallow the loss deduction.

Don't forget about the primary residence exclusion! If this was your brother's primary residence for at least 2 of the 5 years before the sale, he might qualify to exclude up to $250,000 of gain from his income (or $500,000 if married filing jointly). Based on what you described, he lived there for about 2 years before moving out 2 years ago, so he might just barely qualify if the timing works out exactly. This could potentially eliminate any tax liability from the sale, even if he has to report it.

This is definitely a tricky situation that requires careful documentation. From what you've described, your brother needs to report the sale even though he didn't receive proceeds from the actual sale, because he was still legally on the deed. The key is treating this as a two-part transaction: (1) the original buyout he received when they split up, and (2) the formal sale that just happened. On Schedule D, he should report the sale with his cost basis being the original purchase price plus improvements, and his proceeds being only the buyout amount he received years ago (not the recent sale proceeds). You'll definitely want to include a detailed explanation with the return describing the situation. Also, try to get documentation of the original buyout agreement if possible - this will support your position if the IRS has questions. One important thing to check: make sure you understand whether he received a 1099-S form. If he did, the IRS will be expecting to see this sale reported. If the ex-girlfriend also reports part of the sale, you want to make sure there's no double-reporting of the same income.

Just adding that besides SSNs, there are other types of TINs too: - EIN (Employer Identification Number) for businesses - ITIN (Individual Taxpayer Identification Number) for non-citizens - PTIN (Preparer Tax Identification Number) for tax preparers - ATIN (Adoption Taxpayer Identification Number) for pending adoptions So while most people's TIN is just their SSN, not everyone's is!

Yes, you can definitely have multiple TINs! As an individual with a business, you'd have your SSN for personal tax matters and an EIN for your business. Many people have both - your SSN identifies you as an individual taxpayer, while your EIN identifies your business entity. You'll use your SSN on your personal tax return (Form 1040) and your EIN for business-related forms and transactions. Just make sure to use the correct number for the right purpose - SSN for personal stuff, EIN for business stuff.

Filed on February 4th through TurboTax and just got my refund deposited this morning! That's exactly 24 days from filing. I was also claiming child tax credit for my son and had been stuck on "processing" status until yesterday when it finally updated to "approved." Reading through this thread over the past few days really helped manage my expectations - seeing Jackie's timeline of 23 days with both EIC and child tax credit made me realize I was still well within the normal range. For everyone still waiting who filed around the same time and are claiming child tax credits, it looks like we're all hitting that 23-25 day window pretty consistently. The WMR tool really doesn't update until the very end, so don't stress too much about it showing "processing" - mine only changed to approved about 36 hours before the money actually hit my account. Hang in there everyone, your refunds should be coming through any day now!

I filed on February 8th through H&R Block and just wanted to add my timeline to help others who are waiting. I'm claiming child tax credit for my daughter and standard deduction with W-2 income. Got my refund deposited yesterday - that's exactly 22 days from filing date. Like everyone else mentioned, the WMR tool was completely unhelpful and stayed on "processing" until literally the day before my refund hit. I was getting really anxious around day 18-19 thinking something was wrong, but reading similar threads like this one really helped me understand that returns with child tax credits are just taking the full processing window this year. For anyone still waiting who filed in early February with child tax credits - based on all the timelines shared here, it looks like we're consistently seeing 22-25 days, so hang in there! The "processing" status doesn't mean there's an issue, it's just the IRS working through their normal queue.

As a newcomer to this community, I want to thank everyone for this incredibly comprehensive discussion! I'm dealing with a very similar situation - about $85k in contractor payments made through various apps including Venmo and PayPal. What really helped me understand this issue was the legal breakdown from the tax attorney who explained the distinction between IRC Section 6041 (1099-NEC requirements) and IRC Section 6050W (1099-K reporting). These serve completely different purposes, and my obligation as a business paying for services doesn't change based on the payment method I used. The audit risk perspective shared by multiple members really drove home why compliance is so critical. The thought of the IRS seeing substantial contractor expense deductions without corresponding 1099s is definitely concerning, especially when the penalties can be up to $290 per missing form. I'm also dealing with a contractor who's been resistant to providing a W9, claiming app-based payments don't require 1099s. Based on all the advice here, I'm going to send a formal backup withholding notice immediately. Their accountant's misinformation shouldn't put my business at risk. This thread has given me complete confidence to move forward with issuing all required 1099-NECs regardless of payment method. The consensus from tax professionals, experienced business owners, and community members who've been through audits is crystal clear - issue those forms and protect your business!

As a newcomer to this community, I want to add my experience dealing with a very similar situation. I run a consulting business and paid about $110k to contractors through Venmo and PayPal last year. Initially, I was getting completely conflicting advice from different sources about whether payment apps changed the 1099 requirements. Some people told me Venmo payments were exempt, others said I still needed to file 1099-NECs. The confusion was overwhelming! What finally clarified everything for me was understanding that the IRS doesn't care HOW you paid contractors - they care that you paid them for services and reported it properly. Whether I wrote a check in 1985 or sent money through Venmo in 2024, the fundamental reporting requirement is exactly the same. The audit risk perspective really sealed it for me. When I realized the IRS would see $110k in contractor expense deductions on my return and expect to see matching 1099-NECs, it became clear that skipping the forms wasn't worth the risk. The potential penalties alone could cost thousands. I also had one contractor initially refuse to provide a W9, claiming their tax preparer said app payments don't need 1099s. I sent them a formal backup withholding notice explaining that 24% of future payments would go directly to the IRS if they didn't provide their tax information. They suddenly became very cooperative! For anyone still hesitating about this - trust your instincts and issue those 1099-NECs. The payment method is completely irrelevant to your reporting obligations. Better to be fully compliant than deal with penalties and audit headaches later.