As someone new to this community, I'm really grateful to have found such a comprehensive discussion about international creator compliance! This thread has been incredibly educational. I wanted to share a perspective that might be helpful - your cousin's situation actually highlights a common challenge that many young international creators face, and the systematic approach everyone has outlined here could genuinely help others in similar situations. The key points that really stand out to me are: getting the ITIN application started with proper parental involvement, being completely transparent with TikTok about the VPN usage from the beginning (rather than waiting for them to discover it), and making sure to get professional tax advice that covers both US requirements and home country implications for minors. One thing I'd add is that while this process might seem daunting now, your cousin is actually in a great position by addressing this properly at age 16. Learning to navigate complex business and tax requirements early in her creator journey will give her such a solid foundation for long-term success. Many creators try to handle these compliance issues after they've already built significant income streams, which makes everything much more complicated. The waiting period during ITIN processing could also be a blessing in disguise - she can focus on content quality and audience building so she's in an even stronger position when monetization gets approved. Sometimes being forced to slow down and do things the right way leads to much better outcomes! Best of luck to your cousin and her family in navigating this process properly!

As someone who's worked in international tax compliance, I want to emphasize how refreshing it is to see this thread focus on legitimate solutions rather than shortcuts. Your cousin's situation is actually quite common, and the systematic approach everyone has outlined here is absolutely the right way forward. One additional consideration I'd mention is that once your cousin gets her ITIN and starts receiving payments, she should be prepared for quarterly estimated tax payments if her earnings exceed certain thresholds. The IRS expects regular payments throughout the year, not just annual filing, so setting aside a percentage of each TikTok payment into a separate tax account will prevent any surprises. Also, regarding the VPN disclosure to TikTok - I'd recommend having her parents frame it as "learning about compliance requirements" rather than admitting to intentional circumvention. The key is showing that you're now committed to doing everything properly moving forward. The waiting period really is an opportunity. She can use this time to study successful creators in her niche, improve her content strategy, and maybe even start building an email list or other owned media channels. These foundational business skills will serve her incredibly well once monetization is approved. Your cousin is fortunate to have family support in navigating this properly. The legitimate foundation you're building now will protect her throughout her entire creator career!

Am I the only one who thinks the 1099-K threshold being lowered is the absolute worst? Now I have to deal with all these discrepancies when before I just reported my income and paid my taxes without all this confusion. I have 3 different payment processors and each one seems to calculate the 1099-K differently. One includes refunds, one doesn't. One includes the fees, one doesn't. It's a nightmare to reconcile!

I completely understand your frustration with the 1099-K discrepancies - this is unfortunately very common with digital businesses using multiple payment processors. Here's what you need to know: You should report your GROSS sales revenue on Schedule C, not the 1099-K amount or the net amount. So in your case, that would be the $59,106.25 from your Square revenue report. Then deduct the $2,127.93 in processing fees as a business expense under "Commissions and fees" on Schedule C. The discrepancy between your gross revenue ($59,106.25) and the 1099-K amount ($58,215.75) could be due to several factors: timing differences (transactions processed in different calendar periods), refunds that were included differently, or chargebacks. I'd recommend calling Square directly to get clarification on this specific difference. For Teachable reporting net amounts - this varies by platform. Some report gross payment amounts, others report what they actually paid out to you. The key is consistency in how YOU report it: always use gross sales as income, then deduct all fees and platform costs as business expenses. Keep detailed records showing your calculation methodology. If there's ever a question from the IRS, you'll be able to demonstrate exactly how you arrived at your reported income figures and why they might differ slightly from your 1099-K amounts.

One thing I'd add to all the great advice here - if you're dealing with an inherited property loss, consider whether you might have any other capital gains this year that could offset the loss. I inherited my grandmother's house and sold it at a $40k loss, but I also had some stock gains from earlier in the year. The capital loss from the house sale completely offset those gains, saving me a significant amount in taxes. Also, if your loss is larger than what you can use this year (after offsetting gains and taking the $3k against ordinary income), remember that unused capital losses carry forward indefinitely. So even if you can't use the full $55k this year, you can keep applying $3k per year against ordinary income until it's used up, or use it to offset future capital gains. Make sure to keep detailed records of how much loss you've used each year so you can track your remaining carryforward balance. The IRS doesn't send you reminders about this!

Great question! I dealt with a very similar situation when I inherited my aunt's property last year. The key thing to understand is that your stepped-up basis is indeed the $850k appraised value at the date of death, so you absolutely can claim that $55k as a capital loss. One important detail to double-check: make sure you're including ALL allowable selling expenses when calculating your loss. Beyond the obvious ones like realtor commissions and closing costs, you might also be able to deduct things like title insurance, escrow fees, any inspection costs you paid for, and even some of the minor repairs if they were specifically done to facilitate the sale. I'd recommend getting a copy of IRS Publication 544 (Sales and Other Dispositions of Assets) - it has a section specifically about inherited property that's really helpful. The loss gets reported on Form 8949 first, then carries over to Schedule D. Also worth noting: if this is your first time dealing with inherited property taxes, consider having a tax professional review everything before you file. The rules can be tricky, and you want to make sure you're maximizing your allowable deductions while staying compliant.

Just wanted to add another perspective here - I work as a tax preparer and see this situation a lot with clients. One thing that often gets overlooked is that some states have "safe harbor" rules for part-year residents that can actually work in your favor. Since you sold the stocks while still an Oregon resident, Oregon will definitely tax those gains. But here's something to consider: make sure you're taking advantage of any credits for taxes paid to other states. When you file your Colorado return, you should be able to claim a credit for taxes paid to Oregon on the same income, which prevents true double taxation. Also, document everything about your move timeline. Colorado may want to see proof of when you actually established residency there - utility bills, lease agreements, employment start date, etc. This helps establish the clear cutoff date for which state taxes which income. The $65k gain is substantial enough that it's probably worth consulting with a tax professional who specializes in multi-state returns, especially since Oregon and Colorado have different rules about how they treat capital gains.

This is a really complex situation, and you're smart to be thinking about it now before tax season hits. From what I understand, since you were still an Oregon resident when you sold those stocks, Oregon will likely claim the right to tax the entire $65k in capital gains at their rates. One thing that might help ease your stress - when you file as a part-year resident in both states, each state typically only taxes the income earned while you were actually living there. So Colorado shouldn't double-tax those gains since they were realized before you moved there. The timing is unfortunate from a tax perspective since Oregon treats capital gains as regular income (so potentially higher rates), but what's done is done. For future reference, this is exactly why some people delay major asset sales until after they've established residency in lower-tax states. My advice would be to start gathering all your documentation now: the exact dates of your move, employment start date in Colorado, when you closed on housing, utility transfers, etc. You'll need this to clearly establish your residency timeline for both states. Given the size of those gains, it might be worth consulting with a tax pro who handles multi-state returns - the cost will probably be worth it to make sure you're not leaving money on the table or missing any deductions.

This entire thread has been absolutely invaluable! As someone who's been dreading dealing with my first IRA withdrawal precisely because of the estimated tax confusion, I can't express how much clarity everyone has provided. I'm particularly struck by how the real-world experiences shared here - especially Mary's detailed walkthrough and the tax professional's technical explanation with the IRC citation - have made what seemed like an impossibly complex tax situation suddenly feel manageable. The December withdrawal with direct withholding strategy appears to be exactly what I need. What really stands out to me is how this approach eliminates the guesswork and quarterly payment stress while keeping everything above board with the IRS. The fact that the withholding is treated as if paid throughout the year (even from a December distribution) is such a elegant solution to what I thought was going to be a nightmare of quarterly calculations. I'm planning to implement this strategy for my situation: call my custodian (Fidelity) in November to understand their year-end processing timeline, submit my withdrawal request in early December with 20-22% federal withholding, and finally stop losing sleep over estimated tax obligations. For anyone else who's been intimidated by this process like I was - this thread proves that sometimes the simplest, most straightforward approach really is the best one. Thanks to everyone who shared their knowledge and experiences!

As someone who just went through my first IRA withdrawal using the strategy discussed here, I wanted to share my experience to hopefully help others who might be hesitant about this approach. I was in almost the exact same situation as Miranda - retired, living on Social Security and some investment income, and completely overwhelmed by the estimated tax requirements for IRA withdrawals. After reading through all the great advice in this thread, I decided to try the December withdrawal with direct tax withholding approach. Here's how it went for me: I called my custodian (T. Rowe Price) in early November to understand their year-end procedures. They told me their internal cutoff for guaranteed same-year processing was December 18th, and their online withdrawal form made it very easy to specify withholding percentages. I submitted my request on December 8th with 20% federal withholding, and the funds were in my account by December 19th. The whole process was incredibly smooth and stress-free compared to what I had been imagining. When I filed my taxes this year, the withheld amount appeared correctly on my 1099-R in Box 4, and I actually ended up with a small refund since I had slightly overwitheld to be safe. For anyone still on the fence about this approach - it really does work exactly as described here. The key is just planning ahead with timing and being clear about your withholding preferences with your custodian. Much simpler than quarterly estimated payments!