This is a great question that trips up a lot of people starting collectibles businesses! The distinction between dealer and collector status is crucial for tax reporting. Since you're planning to operate as a business (regularly buying and selling for profit), you'll likely be considered a dealer, which means Schedule C reporting. Your coins would be treated as inventory, and profits would be ordinary business income rather than capital gains. However, there's an important nuance: you can potentially have both dealer AND collector activities. If you clearly segregate certain coins as personal investments (not for resale), those specific items could qualify for Schedule D treatment when sold. The key is documentation - you need to establish your intent at the time of purchase and maintain clear records. For your eBay business setup, I'd recommend: 1. Keep detailed records of all purchases with dates, costs, and intent (business inventory vs personal investment) 2. Use separate storage/tracking for any coins you designate as investments 3. Consider consulting with a tax professional familiar with collectibles businesses before you start The IRS looks at factors like frequency of sales, time spent on the activity, expertise in the field, and profit motive to determine dealer vs collector status. Starting with proper documentation will save you headaches later!

Another important consideration is quarterly estimated tax payments if your business becomes profitable. Since you'll be self-employed with this coin business, you'll likely need to make quarterly payments to avoid underpayment penalties. The IRS generally expects you to pay at least 90% of your current year tax liability or 100% of last year's liability (110% if your prior year AGI was over $150K) through withholding and estimated payments. For a new business, I'd recommend setting aside about 25-30% of your net profits in a separate account for taxes - this covers federal income tax, self-employment tax (Social Security and Medicare), and potentially state taxes. You can use Form 1040ES to calculate and make these payments quarterly. Also, don't forget you can deduct legitimate business expenses like eBay fees, PayPal fees, shipping supplies, storage costs, photography equipment for listing photos, and even a portion of your home if you use it exclusively for business storage or office space (home office deduction). Keeping detailed records of all these expenses will help reduce your tax burden significantly.

Does anybody know if the "undetermined term" status affects the actual tax rate you pay? Or is it just an issue of which form/section to report it on? My broker labeled a bunch of my crypto transactions this way and I'm trying to figure out if it actually matters for how much tax I owe or just for paperwork purposes.

I've dealt with this exact situation and want to emphasize something important: when you have undetermined term transactions, the IRS expects you to make a reasonable effort to determine the actual holding period rather than just defaulting to short-term treatment. Here's my recommended approach: First, gather any records you can find - old statements, trade confirmations, even bank records showing when funds were transferred for purchases. Second, if you're missing some information, create a spreadsheet documenting what you know and your methodology for estimates. Third, when in doubt, consider using Form 8949 with the appropriate adjustment codes to explain your situation. One thing I learned the hard way: if you report everything as short-term just because it's "undetermined," you might overpay taxes significantly. The IRS won't refund the difference if you later find records showing they were actually long-term holdings. It's worth spending the time upfront to get this right, especially given the substantial difference in tax rates between short-term and long-term capital gains. Also, keep detailed records of your research process in case of questions later. The IRS appreciates good faith efforts to comply accurately.

i worked at a big tech company using the double irish setup and honestly the amount of resources devoted to tax avoidance was insane. we had entire teams just for moving IP around between jurisdictions the craziest part is how normalized it was. nobody even questioned if we should be paying more taxes, just how to legally avoid them. when ireland announced the phase-out there was this huge scramble to develop new structures. already had plans b, c, and d ready to go so even with this oecd thing, i'm super skeptical. these companies are always 3 steps ahead of regulators. as soon as one loophole closes they've already found three more.

As someone who's been working in tax compliance for over a decade, I think there's actually reason for cautious optimism this time. The OECD approach is different because it's coordinated globally - previous efforts failed partly because countries acted unilaterally and companies could just move to non-participating jurisdictions. What's encouraging is seeing how quickly major economies adopted Pillar Two. The EU, UK, Canada, Japan, and others are already implementing or have committed to the 15% minimum tax. Even traditional tax havens are joining because they risk being shut out of the global system if they don't participate. That said, you're absolutely right that corporations will adapt. I'm already seeing clients explore structures involving digital services taxes, carbon credits, and R&D incentives that might reduce their effective rates while staying technically compliant. The arms race continues, but at least now there's a global floor rather than a race to the bottom. The real test will be enforcement and whether countries actually collect the "top-up" taxes when companies pay less than 15% elsewhere. Implementation details matter enormously here.

I've been lurking on this thread because I'm facing the exact same nightmare! Reading through everyone's strategies has been incredibly helpful. I've been trying to reach the TPP line for 6 days now with zero success - just endless busy signals and disconnections. What's really frustrating is that I have no idea WHY I was flagged for identity verification. Like Ravi mentioned, I triple-checked everything before filing. I even used the same tax software as last year with identical information sources. It's maddening to be stuck in limbo without knowing what triggered the hold. I'm going to try the Tuesday 7:03am strategy that Aisha shared - the logic about avoiding the 7:00am rush makes perfect sense. I've been part of that problem calling right at opening! Also planning to gather every document from the past 3 years tonight, including old address info. One question for those who successfully got through - did the agents give you any insight into what actually triggered your identity verification in the first place? I'm curious if there are common patterns we should know about to potentially avoid this in future years. Thanks to everyone sharing their experiences and strategies. It's reassuring to know I'm not alone in this bureaucratic maze! 🤞

I just successfully got through yesterday after reading this thread! Used the Tuesday 7:03am strategy and it WORKED - connected after 67 minutes on hold. Here's what I learned that might help others: The agent told me my verification was triggered because I filed significantly earlier than usual (normally file in April, filed in February this year). Apparently their system flags "behavioral changes" even if everything is correct. **Key preparation tips:** - Have your actual Social Security card in hand, not just the number memorized - Print out your last 3 years of returns - they asked for specific line items from 2022 and 2021 - Know your previous addresses WITH zip codes - they were very specific about this - If married, have your spouse's info ready too (they asked for my husband's mother's maiden name!) **During the call:** - The verification took 18 minutes once connected - Agent was actually very patient and helpful - She explained each step of what she was doing - Confirmed my return would process within 6 business days **Mental health tip:** I put the call on speaker and did yoga stretches during the hold time. Made the wait so much more bearable than sitting there stewing in frustration! To everyone still trying - don't give up! This thread gave me hope when I was ready to throw my phone at the wall. Your persistence will pay off! 🙌

This is such a helpful thread! I'm dealing with a similar situation with my son's Coverdell ESA. One additional consideration I discovered is the timing of when you do the Coverdell-to-529 rollover within the tax year. My tax preparer pointed out that if you roll the Coverdell funds to a 529 late in the year, you might miss the window to use any of those funds for qualified education expenses in that same tax year (if your beneficiary is still in school). This could be relevant if you're trying to maximize the educational use of the funds before eventually converting to Roth. Also, for anyone considering this path, make sure to keep detailed records of the original Coverdell contribution dates and amounts. Even though they don't carry over to the 529 for the 15-year rule, you'll want this documentation for your own tax planning and to verify any calculations your financial institution makes. The complexity of these rules really makes me appreciate having professional guidance, whether that's through tax software, advisors, or the various services people have mentioned here!

Thank you all for this incredibly detailed discussion! As someone who's been wrestling with a similar Coverdell ESA situation, this thread has been a goldmine of information. I wanted to add one more consideration that my CPA brought up - the impact of Required Minimum Distributions (RMDs) on this strategy. Since Roth IRAs don't have RMDs during the owner's lifetime, converting unused education funds to a Roth can be a great long-term estate planning tool. However, if you're planning this conversion for a young beneficiary, you need to factor in that they'll eventually have RMDs from any traditional retirement accounts they accumulate. The timing of when to do these conversions (once the 15-year period is satisfied) might be strategic - doing them during years when the beneficiary has lower income could minimize the tax impact, since the conversions count as taxable income. Also, I noticed several people mentioned state tax implications. Don't forget that some states don't tax Roth IRA distributions at all, while others do. So the long-term state tax treatment of the converted funds could be another factor in deciding whether this strategy makes sense for your situation. The complexity of all these rules really reinforces why getting professional guidance is so valuable for these decisions!