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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.
One thing that hasn't been mentioned is that there's a crucial difference between RSUs (Restricted Stock Units) and ESPPs. With RSUs, there's typically withholding at vesting because that's a taxable event (ordinary income). With ESPPs, taxation gets more complicated. If your ESPP has a "lookback provision" where you get to purchase at a discount from either the beginning or end of the offering period (whichever is lower), there can be additional tax implications. The discount is always taxable as ordinary income, but depending on whether you do a qualifying or disqualifying disposition, the timing and treatment of taxes varies. From what you've described, it sounds like your company might be withholding for the discount portion, but calling it capital gains tax, which is confusing you. I'd ask for documentation that specifically explains what portion of your purchase is being taxed and under what section of the tax code.
Can you explain what a "qualifying or disqualifying disposition" means? The tax document they sent me does mention something about a "disqualifying disposition" but doesn't explain what that means.
A qualifying disposition means you held the ESPP shares for both: 1) at least 1 year after the purchase date, and 2) at least 2 years after the offering date (when the purchase period began). If you meet both holding periods, you get more favorable tax treatment. A disqualifying disposition means you sold before meeting either of those holding periods. In that case, the entire discount gets taxed as ordinary income. It's strange they're mentioning "disqualifying disposition" if you haven't sold yet. That term typically only applies when you actually sell the shares. This reinforces my suspicion that there's a communication problem or misunderstanding with your benefits department. I'd specifically ask them why they're referencing a disqualifying disposition when you still hold the shares.
Has anyone considered that this might actually be a prepayment of taxes that the company is facilitating, rather than requiring? Some companies offer this as a service to help employees avoid a big tax bill later. If the ESPP discount is substantial, or if there was a big jump in stock price during the offering period, there could be a significant taxable event even before selling. The company might be offering to withhold taxes now to help spread out the impact rather than having employees face a surprise tax bill next April. I'd ask if this withholding is mandatory or optional. If it's optional, it might actually be a beneficial service they're providing.
This is an excellent point. My company does something similar - they provide an optional tax withholding program for equity compensation. They calculate the projected tax impact and let us choose whether to have extra withholding throughout the year. It's actually really helpful for cash flow management.
One thing to consider - how did you pay the rent? If you paid it from a joint account where your roommate/fiance also contributes, then technically they could argue your fiance did indirectly pay part of the rent. But if you paid from your personal account and your fiance never transferred money to you for rent, then you have a stronger case. Also, this might not be worth fighting too hard if you're getting married in two months. Depending on your state, married couples often combine their property tax refunds anyway, so it might all come out in the wash next year.
All the rent payments came directly from my personal checking account. My fiance and I keep our finances completely separate for now - they pay for utilities and groceries, I cover the rent. So there's a clear paper trail that I'm the only one who paid rent. I hear what you're saying about it maybe not being worth fighting since we're getting married soon, but we're filing separately this year and potentially leaving several hundred dollars on the table with this incorrect CRP. My state has a pretty generous rent credit program.
In that case, you definitely have solid grounds to get this corrected. Since you have a clear paper trail showing you made 100% of the payments from your personal account, the CRP should reflect that. Several hundred dollars is absolutely worth pursuing. I'd recommend following the advice others have given about submitting a dispute. Make sure to include bank statements showing the payments came from your account, and be persistent with your landlord - they should want to avoid potential issues with the tax authorities by providing accurate documentation.
Has anyone dealt with this in Minnesota specifically? The CRP form there (CRP certificate) seems especially strict and my landlord is telling me the same thing - that they can't change it because "the system" automatically splits it between everyone on the lease.
Minnesota resident here - your landlord is not correct. The MN Department of Revenue is very clear that CRPs should reflect who actually paid the rent, not just who was on the lease. I had this issue two years ago and ended up calling the MN DOR directly. They told me to file Form M-1PR with an explanation and my payment proof. Got my full refund about 6 weeks later.
Something no one's mentioned yet - have you looked into setting up an S-Corp election for your LLC? At your income level, it might save you significant self-employment taxes. With an S-Corp, you'd pay yourself a reasonable salary (subject to FICA taxes) and take the rest as distributions (not subject to self-employment tax). Could save you thousands depending on your situation.
I've heard about the S-Corp option but wasn't sure if my income was high enough to make it worth the extra paperwork and accounting costs. What's considered the breakeven point where it starts making sense financially?
The breakeven point varies depending on your specific situation and local costs, but generally around $40,000-60,000 in profit is where many tax professionals suggest considering it. At your $52,500 income level, you're in that range. The main calculation is comparing what you'll save in self-employment taxes versus the additional costs. You'll need to file Form 1120-S annually, likely pay for payroll services (roughly $50-100/month), and possibly higher accountant fees. Most people find it worthwhile when they can save at least $2,000 annually in taxes after covering these extra expenses.
Don't forget to check if you qualify for the Qualified Business Income (QBI) deduction! As a sole proprietor, you might be able to deduct up to 20% of your qualified business income. This is a big tax break that a lot of people miss.
The QBI deduction is amazing but gets complicated fast. I thought I didn't qualify but my tax person found a way to make it work by adjusting some of my expense categories. Ended up saving almost $2k last year!
Bethany Groves
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.
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Skylar Neal
ā¢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?
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Bethany Groves
ā¢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.
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KingKongZilla
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).
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Rebecca Johnston
ā¢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!
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