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Something else to keep in mind - don't just think about the IRS deadline. If you're filing state returns too, each state can potentially have different rules about their e-file cutoff times. Most follow the federal guidelines, but there are exceptions. I learned this the hard way when I had a California return accepted by the IRS but rejected by the state for being "late" even though I submitted everything at the same time.
Do you happen to know which states have different deadlines? I'm working on returns for clients in multiple states and now I'm worried...
I don't have a comprehensive list, but I know California strictly enforces their own cutoff time. New York and Illinois have occasionally had different timing requirements too, especially during extension periods. The safest approach is to check each state's department of revenue website directly. Most will have a specific notice about e-filing deadlines on their homepage this time of year. If you can't find clear information, finish those multi-state returns at least 24 hours before the federal deadline to be safe.
Has anyone had issues with the tax software itself crashing due to high volume? Last year I was filing with TurboTax and their servers got super slow around 10pm on deadline day. Took almost an hour just to transmit a return that normally takes minutes.
I use Koinly for tracking all my crypto transfers and it automatically tags them as non-taxable events. Been using it for 3 tax seasons now and it generates all the forms I need for filing. Just another option to consider.
The price depends on how many transactions you have annually. I'm on the $99 plan which covers up to 1,000 transactions per tax year. They have cheaper options if you have fewer transactions and more expensive if you're a heavy trader. I've found it worth it because it automatically categorizes everything correctly - transfers, trades, income from staking, etc. You can also manually edit any transactions if needed. At tax time, it generates all the forms needed for filing including Schedule D and Form 8949.
Anyone know if hardware wallets like Ledger complicate this? I transfer from Coinbase to my Ledger for security, then sometimes back to an exchange if I want to sell.
As someone who runs an Amazon FBA business from Japan with a Wyoming LLC (similar to your setup), here's what I've learned: The 1099-K is reporting the payments processed through Shopify Payments, but that's just your gross revenue. The key is properly documenting ALL your expenses. Since you're shipping directly from China, make sure you have proper documentation for COGS, including manufacturing, shipping, and any duties paid. For Wyoming specifically - yes, no state income tax, but you still need to file an annual report and pay the $60+ annual fee to maintain good standing. One thing to watch for: if your US company is just a "paper entity" and all real work happens in China, the IRS might question if you have "nexus" in the US at all. This could either help or hurt depending on your situation.
Thanks for this info! What do you mean by "paper entity" and the nexus issue? Our company is registered in Wyoming, has a registered agent there, and a US bank account, but all actual operations (including me as the owner/operator) are in China. Could this cause problems?
The "nexus" issue refers to where your business has sufficient presence or connection for tax purposes. If all actual business activities (management, operations, inventory) are in China, the IRS could potentially view the business as a foreign entity despite the US registration. This could work both ways. If determined to be a foreign entity, you might only need to report US-sourced income to the IRS, potentially reducing your tax burden. However, it could also trigger complex reporting requirements like Form 5471 for foreign corporations. To strengthen your US nexus, consider: maintaining a US phone number, having some business activities conducted in the US (even if remotely), using US-based services, and clearly documenting the business purpose of your US entity. Having just a registered agent and bank account might be seen as insufficient to establish true US operations.
Don't forget about FILING THRESHOLDS for the 1099-K! This is important and changed recently. For 2023 taxes (filing in 2024), the threshold is still $20,000 AND 200 transactions. But starting with 2024 taxes (filing in 2025), it drops to just $5,000 with NO transaction minimum. If your 1099-K is reporting less than the threshold amount for the applicable tax year, you technically weren't supposed to receive it. But now that you did, you still need to report that income (but can offset with expenses).
Actually, this information isn't quite right. The $600 threshold was supposed to take effect for 2023 taxes (filing in 2024), but the IRS delayed it. They've announced another delay for the 2024 tax year too. So the $20,000 AND 200 transactions threshold is still in effect for both years. I just want to make sure nobody's confused when filing!
One thing nobody's mentioned is that if your wife's ITIN is only being used on a joint return with your SSN, you might be able to just attach the W-7 renewal form and her ID docs directly to your tax return when you file instead of doing it separately beforehand. That's what we did last year. Just make sure you're using a tax preparer who knows how to handle ITIN renewals (not all of them do). We learned this the hard way after trying three different preparers!
Thanks for this tip! Do you remember approximately how long it took to process both the tax return and ITIN renewal when you did it this way? I'm wondering if it delays the refund significantly.
When we did it this way, the whole process took about 11 weeks total - definitely longer than a regular tax return. Our refund was held until the ITIN was fully processed. If you're counting on getting your refund quickly, you might want to do the ITIN renewal separately before filing. I'd also add that the IRS sent us a letter about 4 weeks after filing to confirm they received the ITIN renewal application, which gave us some peace of mind during the wait.
IMPORTANT: Make sure your wife's name on the ITIN application EXACTLY matches her ID documents. My wife's middle name was spelled slightly differently on her passport vs birth certificate and our renewal got rejected. Had to resubmit everything and it delayed the whole process by months. Also if you're mailing original documents, use a trackable shipping method!! We sent her passport and freaked out for weeks not knowing where it was until it finally came back.
Fatima Al-Hashemi
For a more visual approach, I found "The Complete Guide to Your Personal Finances Online" by Scott Bilker really helpful. It has flowcharts and decision trees that make the tax code more visual. The book has a whole section on real estate with clear examples showing how different scenarios affect your tax liability.
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Dylan Mitchell
ā¢Does it cover more recent tax law changes like the TCJA and SECURE Act? I've found many tax books become outdated quickly when tax laws change.
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Fatima Al-Hashemi
ā¢It does cover TCJA changes pretty thoroughly, especially how they impact real estate investors with the new QBI deduction and business interest limitations. The SECURE Act coverage is more limited though, mainly focusing on the elimination of the stretch IRA and changes to RMD ages. The publisher does offer annual updates on their website that cover more recent changes, which helps keep the content relevant even as tax laws evolve. I've found this combination of the book plus the online updates works better than waiting for completely new editions.
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Sofia Martinez
Have u guys tried any of the tax softwares like TurboTax or H&R Block? They basically walk u thru everything step by step and explain the tax code as u go. Might be cheaper than buying a bunch of books?
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Dmitry Volkov
ā¢I've used both. They're good for filling out forms but terrible for actually understanding the tax code. They just tell you what to do without explaining why or how things work together. Fine if you just want to file, useless if you want to learn and optimize.
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