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Here's an important thing to know about K-1s that nobody mentioned yet - they often arrive LATE! Like after April 15th late. If that happens, you'll need to file an extension (Form 4868). Your brother should be able to give you an estimate of the numbers so you can pay any estimated tax due with your extension request. I invest in several partnerships and literally never get my K-1s before April. It's annoying but normal.
Does filing an extension because of a late K-1 increase your chances of being audited? I've always heard you should avoid extensions if possible.
Filing an extension does not increase your audit risk at all. That's a common myth. In fact, tax professionals file extensions for many of their clients as standard practice. The key is making sure you pay any estimated tax due when you file the extension. Penalties are for not paying on time, not for filing the actual return later. As long as you make a good faith estimate of what you owe and pay that amount with your extension request, you're completely fine.
WARNING about K-1s - make sure the EIN on the form matches your brother's business! I got a K-1 last year that had a typo in the EIN and it caused my return to be rejected when I e-filed. The IRS computers couldn't match my reported K-1 info with what the business filed. Also check if your state requires you to attach a copy of the K-1 to your state return. Some states do require this while the federal return doesn't.
This is great advice! I had the same issue with a wrong EIN and it was a nightmare to fix. I'd also recommend comparing the K-1 you receive with any estimated K-1 info your brother might have given you during the year. If there are big differences, ask why before filing.
Quick note about using PayPal specifically - they've lowered their reporting threshold to $600 as of last year. So even fairly small amounts of side income will trigger them to generate a 1099-K. Also, PayPal has been known to freeze accounts that they suspect are used for certain types of content sales. You might want to look into platform-specific payment options that cater to content creators as an alternative.
That's really good to know about the account freezes! Do you know if other payment platforms like Venmo or Cash App have similar issues? Or would you recommend something completely different?
Venmo is actually owned by PayPal so they have similar policies. Cash App can be more flexible but still has its limitations. Many content creators use platforms specifically designed for their industry that have built-in payment processing - these tend to be much more stable since they're designed for that purpose. Some also use multiple payment methods to diversify risk. Another option is to set up a proper business entity (like an LLC) and get a business bank account. This provides an additional layer of separation between your personal finances and business activities, and gives you more professional payment options. It costs a bit to set up but provides much better protection and legitimacy.
I don't see anyone mentioning quarterly estimated taxes yet! This is super important. If you're making consistent money from self-employment (including selling content online), you need to make estimated tax payments throughout the year. The IRS expects you to pay as you earn, not just at the end of the year. If you wait until April to pay everything, you might get hit with underpayment penalties.
Have you considered using a mail forwarding service that provides a physical address? I use one in Wyoming through a company called Wyoming Mail Forwarding for my e-commerce business. For about $200/year, I get a real physical address (not a P.O. box) that I can use for my business. They scan all mail, and I can decide what to forward to wherever I'm currently staying. The key is understanding that having an address is different from having nexus. If you're truly remote and don't have inventory, employees, or significant sales in a particular state, you might be able to avoid nexus there. But be carefulβeconomic nexus laws vary by state and many now have sales thresholds that can trigger tax obligations regardless of physical presence.
Do these mail forwarding services actually hold up if you get audited? I'm worried about setting something up that looks fishy to tax authorities.
Mail forwarding services are completely legal and legitimate for business addresses when properly used. The key is transparency and accuracy in your tax filings. You need to be truthful about where business activities actually occur, regardless of your official address. If you're audited, what matters is where you're conducting business operations, not just where your mail goes. If you claim Wyoming for tax purposes but are clearly operating from Connecticut, that would be problematic. However, many digital businesses can legitimately operate from anywhere. Document your work locations, keep records of travel, and consult with a tax professional to ensure you're handling multi-state issues correctly.
I went through exactly this last year. Ultimately chose Wyoming because: 1) No state income tax 2) No franchise tax (unlike Texas) 3) Strong privacy laws for owners 4) Relatively low registered agent fees I used a company called Wyoming Corporate Services that provided both registered agent service AND a physical address I could use for business purposes. Cost about $350/year total. One thing nobody mentioned - if you're planning to take investment soon, sophisticated investors will see through attempts to avoid state taxes if you're clearly based elsewhere. Focus on proper compliance rather than extreme tax avoidance. I ended up having to file as "foreign entities" in states where I had actual nexus anyway.
Thank you for sharing your experience! Great point about investors potentially seeing through tax avoidance strategies. Did you end up having to register as a foreign entity in multiple states despite having your Wyoming address? Were there any complications with banking or receiving payments with this setup?
Yes, I did end up registering as a foreign entity in California because I spent significant time working there (over 183 days). The Wyoming address wasn't an issue for banking - I used Mercury for business banking and everything was set up online. They just required my EIN, formation documents, and operating agreement. For payments, no complications at all. Most payment processors and platforms don't care about your physical address as long as you have proper business documentation. The biggest challenge was actually keeping track of where I was working throughout the year for tax purposes. I created a simple spreadsheet to log my location each week, which helped tremendously when tax season came around.
Has anyone done a reverse 1031 exchange? I'm in a competitive market and found the perfect replacement property but haven't sold my current one yet. I heard you can buy first then sell, but it seems complicated.
I did a reverse exchange last year. It's definitely more complex and expensive. You need an Exchange Accommodation Titleholder (EAT) to hold the new property while you sell the old one. My qualified intermediary charged about $7K more for this vs a standard exchange. You still have 180 days total to complete everything, but now you're racing to sell your property. If you can't sell in time, you lose the exchange benefits.
Quick question about the 1031 exchange timeframe - does the 45-day identification period include weekends and holidays? My closing date is April 1, 2025, so would my identification deadline be May 16 or would it be later if there are holidays?
Brooklyn Foley
Don't overlook the possibility that your ownership situation might have changed over the years. I had a similar dispute with my accountant about Form 5471, and it turned out we were both partially right. In my case, there had been a corporate restructuring at the foreign company that slightly changed the ownership percentages, pushing US ownership temporarily over 50% for one tax year. So I did need to file for that year but not for others. Could there have been any changes to the corporate structure or ownership percentages that your CPA is aware of that might have triggered the filing requirement, even temporarily?
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Avery Saint
β’That's an interesting point! I've owned exactly 50% since the beginning with no changes to the ownership structure. The only change in my situation was becoming a US tax resident 4 years ago (I filed the 5471 that first year as required when acquiring stock as a US person). After that, there have been zero changes to ownership percentages or corporate structure.
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Brooklyn Foley
β’Given there haven't been any ownership changes since your initial filing, your analysis looks even more solid. That initial filing when you became a US resident was correct (Category 3 for acquisition), but the ongoing yearly filings wouldn't be required if you don't meet any of the other categories. One more thing to consider - has the foreign corporation ever made any distributions or dividends to you during these years? Sometimes CPAs file Form 5471 if there are distributions because it provides a cleaner way to report them, even if technically not required. Might explain why they've been insistent on filing it.
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Jay Lincoln
The issue might be confusion about the "control" test for Category 4 filers. Some CPAs mistakenly believe that exactly 50% ownership constitutes "control" for Form 5471 purposes, but the IRS definition typically requires MORE than 50% for control. Check Section 957(a) of the tax code - a foreign corp is a CFC if more than 50% of the vote OR value is owned by US shareholders. At exactly 50%, you're right at the edge but don't cross the threshold. Your CPA might be filing "protectively" to avoid potential penalties, but that's an expensive approach if it's not actually required. I'd get a second opinion from a CPA who specializes in international taxation, not just a general tax preparer.
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Jessica Suarez
β’I work with international business structures and this is 100% correct. The control test for Category 4 requires MORE than 50% ownership, not exactly 50%. This is a common misconception among accountants who don't specialize in international taxation. That said, there's a specific rule for closely held companies where two 50% owners might both be considered to have "control" in certain circumstances. This usually applies when both owners are actively involved in management decisions. Is that the case with your foreign corporation? Do you and the other owner make joint decisions, or does one of you have more operational control?
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