This is such valuable information - thank you everyone for sharing your experiences! As someone new to trust administration, I'm dealing with a similar situation where my elderly aunt's irrevocable trust will be distributing assets to my cousins soon. One thing I'm wondering about that hasn't been fully addressed - if the trust has been generating dividend income throughout the years, does that affect the cost basis of the stocks when they're distributed? I know reinvested dividends typically increase your basis, but I'm not sure how that works when it's happening within a trust structure. Also, for those who used the online tools mentioned (taxr.ai), did they help you create a proper paper trail for the basis documentation that Savannah mentioned? That seems like it could be a nightmare to reconstruct years later if not done properly during the distribution. Really appreciate all the practical advice here - it's so much more helpful than trying to decipher IRS publications on my own!

As someone who recently went through a similar trust termination, I want to emphasize a few practical points that might help your brother navigate this smoothly: First, make sure to coordinate the timing of the distribution with your niece's tax situation. Since she'll be inheriting the carryover basis on $115k in unrealized gains, it might be worth considering whether she has any capital losses from other investments that could offset future gains, or if her income will be low enough in the year after distribution to take advantage of the 0% capital gains rate for lower income brackets. Second, don't forget about the trust's final tax year - any income earned from January 1st until the distribution date will need to be reported. This includes dividends, interest, and any capital gains if assets are sold within the trust before distribution. Lastly, I'd strongly recommend having your brother prepare a comprehensive "beneficiary letter" that accompanies the asset transfer. This should include all the basis information, purchase dates, dividend reinvestment history, and any corporate actions. Even if the brokerage provides some records, having everything consolidated in one document from the trustee will be invaluable for your niece's future tax planning. The fact that you're thinking about these implications ahead of time shows you're on the right track. Your niece is lucky to have family members looking out for her financial interests!

INFO: Are you and your boyfriend financially supporting yourselves and your children together, or is your dad providing significant financial support to you? Also, how old are you? The rules are different depending on whether you're over 19 (or 24 if you're a student).

Based on everything you've shared, your dad has absolutely no legal basis to claim you as a dependent. The IRS has very clear rules for this: For a "qualifying child" dependent, you must live with the person claiming you for MORE THAN HALF THE YEAR. Since you haven't lived with your dad at all in the past year, this requirement fails completely. For a "qualifying relative" dependent, the person must provide MORE THAN HALF of your total support. Your dad paying $600/year for car insurance and $50/month for your phone ($1,200 total annually) is nowhere near half of what it costs to support you, your boyfriend, and two children. Your registered domestic partnership establishes that you're part of a separate household unit. You're functioning as a family with your boyfriend and children - this is completely different from being financially dependent on a parent. Tell your dad straight up: "The IRS requires dependents to live with the person claiming them for at least 6 months of the year. Since I haven't lived with you at all, you legally cannot claim me. Period." Don't let him argue with tax law - these aren't opinions, they're federal requirements. If he tries to claim you anyway, the IRS will catch it when returns are processed and he'll face penalties for fraudulent claiming. Protect yourself by filing your own return correctly.

I've been using Credit Karma for my refunds for 3 years now and they're pretty consistent. Usually hits between 2-5am EST on your DDD, sometimes the night before around 10-11pm. Set up those push notifications in the app so you don't have to keep checking! Good luck tomorrow 🤞

Been using Credit Karma for direct deposit for 2 years now. In my experience, they usually post refunds around 3-4am EST on your DDD, but I've gotten lucky a few times and seen it hit around 11pm the night before. The app notifications are clutch - saved me from obsessively checking my balance every hour lol. Hope yours comes through early! 🤞

I'm in a similar boat with my online sales and found this thread really helpful! One thing I'd add is that you should definitely keep track of your selling expenses too - PayPal/platform fees, shipping costs, packaging materials, etc. These are legitimate business deductions even if you don't have perfect inventory records. For your personal collection items, remember that if you're selling things for less than you originally paid (even if you can't prove the exact amount), that's typically not taxable income - it's a personal loss. The IRS generally understands that people aren't running a business when they're just decluttering their homes. I started keeping a simple spreadsheet this year with columns for: item description, where I bought it, approximate purchase price, selling price, and whether it's personal vs business inventory. Even rough estimates with notes about your reasoning are way better than nothing. The key is being consistent and honest about your methodology.

I was in almost the exact same situation last year! The stress is real, but you're already ahead of the game by thinking about this now instead of at tax time. Here's what I learned: the IRS isn't expecting perfection, especially for casual sellers transitioning into more regular online selling. What they want to see is good faith effort and reasonable documentation. For your personal collection items that you've owned for years - if you're selling them for what you think is less than or close to what you originally paid, those often aren't even taxable as income. They're considered personal property sold at a loss or break-even. For the reselling inventory where you don't have receipts, create a simple method and stick to it. I made a spreadsheet documenting my best recollection of costs, noting things like "purchased at XYZ flea market, typical pricing $X-Y for similar items" or "bought from estate sale, estimated cost based on similar items I purchased there." The key is consistency and being able to explain your reasoning. I also started taking photos of price tags or keeping quick voice memos on my phone when buying inventory - makes record keeping so much easier going forward. Don't let the fear paralyze you into overpaying taxes. With some reasonable documentation of your methodology, you should be fine. The IRS understands that many people got caught off guard by the new 1099-K thresholds.

The $3,120 you're paying definitely puts you over the household employee threshold that Josef mentioned. Here's what I learned from my own experience: the key is figuring out if your housekeeper is truly an independent contractor or your employee. Ask yourself: Do you provide the cleaning supplies? Do you tell them what to clean and how? Do you set their schedule? If yes to most of these, they're likely your employee and you need Schedule H, not a 1099. I made the mistake of assuming anyone I paid was automatically a contractor. Turns out the IRS looks at the level of control you have over the work, not just whether you cut them a check. The fact that you're paying through Venmo doesn't change the underlying employment relationship. Since you're new to this, I'd suggest getting clarity on the employee vs contractor question first - that determines everything else about your tax obligations. Better to figure it out now than during an audit later!

I was in the exact same position last year with my housekeeper! The $3,120 annual amount definitely triggers tax obligations, but which ones depend on whether she's your employee or an independent contractor. Here's the simple test I used: If you control HOW the work is done (you provide supplies, set the schedule, direct specific cleaning methods), she's likely your household employee and you need to handle payroll taxes through Schedule H. If she controls her own methods and schedule while you just specify the end result, she's probably an independent contractor requiring a 1099-NEC. The Venmo payments don't change your obligations - they're just documentation of the payments you've made. Since you're over the $2,400 household employee threshold for 2025, this definitely needs to be addressed properly. One thing that helped me was having an honest conversation with my housekeeper about taxes. Many don't realize they should be reporting this income, and getting it documented properly actually helps them build Social Security credits and qualify for things like unemployment benefits. Don't stress too much about being "behind" on this - the IRS is generally reasonable if you're proactive about getting compliant rather than waiting for them to find the issue.