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Great thread! I'm seeing a lot of helpful advice here. Just wanted to add that timing is absolutely critical for the Form 2553 election. Even after you get the state-level corporation established, remember that the S-Corp election must be filed by the 15th day of the 3rd month of the tax year you want it to take effect (March 15th for calendar year taxpayers). If you miss this deadline, you'll have to wait until the following tax year OR request late election relief under Revenue Procedure 2013-30, which requires showing reasonable cause for the delay. The IRS is pretty strict about this timing requirement. Also, make sure all shareholders (including the converted LLP partners who become shareholders) sign the Form 2553. Missing signatures are another common reason for rejection that I've seen in practice.
This is exactly the kind of detailed guidance I wish I had when I first started handling entity conversions! The March 15th deadline is so easy to miss, especially when you're focused on getting the state-level conversion completed first. I've had clients where we successfully converted the LLP to a corporation at the state level but then missed the S-Corp election deadline by just a few days. Having to file for late election relief adds another layer of complexity and uncertainty that nobody wants to deal with. The signature requirement is another gotcha - I always create a checklist now to make sure every single shareholder has signed before submitting. One missing signature and you're back to square one with another rejection notice.
This is such a comprehensive discussion! As someone who's dealt with several entity conversions, I want to emphasize the importance of getting professional guidance early in the process. The two-step conversion process (state corporation formation first, then IRS S-Corp election) is absolutely critical, but there are so many nuances that can trip you up. Beyond the technical filing requirements, you really need to consider the broader business implications that Micah mentioned - liability structure changes, corporate formalities, shareholder restrictions, and exit planning implications. One thing I'd add is to make sure you're documenting everything properly throughout the conversion process. Keep detailed records of the state filing dates, corporate resolutions, and any correspondence with state agencies. This documentation becomes crucial if the IRS has questions about the conversion timeline or if you need to demonstrate reasonable cause for any timing issues. Also, don't underestimate the ongoing compliance burden that comes with S-Corp status. While the self-employment tax savings can be substantial, S-Corps require reasonable salary determinations for shareholder-employees, payroll tax compliance, and more rigorous bookkeeping. Make sure your client understands and is prepared for these ongoing requirements before making the switch.
This is incredibly helpful! I'm new to handling entity conversions and this thread has been a goldmine of information. Alice, your point about documentation is spot on - I can see how having a clear paper trail would be essential if the IRS questions anything down the road. One question I have - when you mention "reasonable salary determinations" for S-Corp shareholder-employees, how do you typically approach that calculation? I've heard the IRS scrutinizes this closely, but I'm not sure what benchmarks or methods are considered acceptable. Is there a safe harbor approach, or does it really depend on the specific industry and role? Also, for someone just starting to handle these conversions, are there any particular resources or guides you'd recommend for staying current on the compliance requirements? I want to make sure I'm not missing anything important for my clients.
Something nobody has mentioned yet - check if your state has more favorable treatment for in-kind donations than the federal government. I'm in Pennsylvania, and our state has some additional deductions for certain types of in-kind professional services to qualifying organizations. Also, while the discount itself isn't deductible, don't forget that all your normal business expenses related to these events are still fully deductible business expenses. You're not getting a charitable deduction, but you are reducing your taxable income by those costs.
That's a really interesting point about state-specific deductions. I'm in California - does anyone know if there are any special provisions here for this type of donation? I'll definitely look into it. And good reminder about the regular business deductions. Sometimes I think I get too focused on the donation aspect and forget the basics!
I don't know California's specific rules, but check with your state's department of revenue website. Many states have realized the value of professional services donations and have created incentives that the federal government hasn't. On the business expense side, make sure you're tracking EVERYTHING related to these discounted events - mileage, meals while working, supplies, even a portion of your phone and internet if you're using them to coordinate these events. Since your profit margin is already reduced by offering the discount, it's even more important to capture all legitimate business expenses.
My husband's consulting company handles this by separating their work into two distinct parts: full-price services rendered (which they get paid for completely) and then they make cash donations completely separate from the service contracts. Works much better for tax purposes and the non-profits still get the benefit. The paperwork is cleaner for both sides too. The non-profits get to report actual cash donations and his company gets the legitimate deduction.
But doesn't that mess with cash flow? Like if I bill $10k but then donate $3k back, I'm paying taxes on that $3k first before getting the deduction, right?
You're absolutely right about the cash flow timing issue. You would pay taxes on the $10k income in the year you receive it, but the charitable deduction might not fully offset that in the same tax year depending on your AGI limits and other factors. One way to handle this is to plan your donations strategically - maybe bunch them in years when you have higher income to maximize the deduction benefit, or spread them out to stay within the AGI percentage limits each year. Some businesses also set aside a portion of payments from these jobs into a separate account specifically for the donations to help with the cash flow management. The timing definitely makes the discount approach more appealing from a cash flow perspective, even though you lose the tax benefit.
This thread has been incredibly educational! I'm actually in a very similar situation - been using margin to buy growth stocks for about 18 months now and just realized I can't deduct any of the interest I've been paying because I have zero investment income. Reading through everyone's experiences, I think I need to get more strategic about this. The covered call approach that Yuki mentioned sounds really interesting, especially since I'm already holding the stocks anyway. And the point about qualified dividend elections is something I definitely need to research more. One question for the group - has anyone tried using bond ladders or Treasury bills as a way to generate consistent investment income? I'm thinking I could allocate maybe 10-15% of my portfolio to fixed income specifically to create a baseline of investment income each year to offset at least some margin interest. The returns might be lower than my growth stocks, but if it lets me deduct thousands in margin interest, the net effect could be positive. Also, for record keeping, I've started using a simple Google Sheet to track my monthly margin interest payments alongside any investment income I receive. Figure it's better to stay organized from the start rather than trying to reconstruct everything at tax time like I did this year! Really appreciate everyone sharing their experiences and strategies. This is exactly the kind of practical advice you can't get from reading IRS publications.
Your bond ladder/Treasury bill strategy is actually really smart! I've been thinking about something similar after reading through this thread. Fixed income might have lower returns, but when you factor in the tax savings from being able to deduct margin interest, the math can work out surprisingly well. One thing to consider with Treasuries is that the interest is exempt from state taxes (if you live in a high-tax state), which could make them even more attractive for this purpose. Even something like a 4-5% Treasury yield becomes more appealing when it's enabling you to deduct margin interest that would otherwise just carry forward indefinitely. I love your Google Sheets approach too! I've been using a similar setup, and it's been a lifesaver for staying organized. The key is being consistent about updating it monthly rather than trying to catch up at year-end. The covered call strategy mentioned earlier is definitely worth exploring once you get comfortable with options. But your bond ladder idea might be a good starting point since it's more straightforward and provides predictable income you can count on for planning purposes.
Great discussion everyone! I'm dealing with this exact issue and have learned so much from reading through all your experiences. One approach I haven't seen mentioned yet is using I Bonds (Series I Savings Bonds) as part of your investment income strategy. You can buy up to $10,000 per year per person, and while the interest compounds tax-deferred until you redeem them, you can elect to report the interest annually as investment income. This could provide a small but consistent source of investment income to offset margin interest, especially if you're married filing jointly (allowing $20,000 in annual purchases). The current I Bond rates are pretty attractive, and since you control when to report the interest income, it gives you flexibility in timing. Plus, unlike the covered call strategy, there's no risk of losing your underlying positions or capping your upside. I'm also planning to implement the Treasury bill ladder approach that Zainab mentioned. Between T-bills, some dividend-focused ETFs, and potentially covered calls on my most stable positions, I should be able to generate enough investment income to start chipping away at my accumulated carryforwards. Thanks to everyone for sharing such practical strategies - this has been more helpful than anything I've found in tax guides!
I went through the exact same frustrating experience with my ITIN application last year! The "missing information" rejection without specific details is unfortunately very common. Here's what I learned from my experience: First, definitely look for a rejection code on your notice - it's usually a small number or letter that corresponds to the specific issue. Sometimes it's easy to miss because it's not prominently displayed. Second, I'd strongly recommend calling the ITIN line (1-800-908-9982) early in the morning - I found I had better luck getting through around 8 AM when they first open. Have your rejection notice and W-7 form ready when you call. For treaty benefits specifically, make sure you're using the correct treaty article and exemption code on your W-7. I initially put the wrong code because I misunderstood which article of the treaty applied to my situation. The IRS website has country-specific treaty tables that show exactly which codes to use for different types of income. Also, since you moved here last year, double-check that your supporting documents (passport, etc.) are still valid and that any required translations are properly certified. Good luck - don't give up! It's worth getting right for the treaty benefits you're entitled to.
This is really helpful advice! I'm in a similar situation as a newcomer and was wondering - when you call that ITIN line at 8 AM, do you typically get through right away or still have to wait on hold? Also, did you end up having to resubmit your entire application package after fixing the treaty code issue, or were you able to just send in a correction? I'm trying to figure out if it's worth attempting the phone call first or if I should just prepare a completely new application package to save time.
Even calling at 8 AM, I usually had to wait 30-45 minutes on hold, but that's much better than the 2+ hour waits I experienced calling later in the day. Sometimes I'd get disconnected and have to try again, which was frustrating. Regarding resubmission - unfortunately, you have to submit a completely new application package. The IRS doesn't accept partial corrections or amendments to rejected ITIN applications. I learned this the hard way when I tried to just send in the corrected treaty code information. They sent it back and told me I needed to resubmit the entire W-7 form with all supporting documents again. My advice would be to call first to get the specific details of what went wrong, then prepare your complete new application package with those corrections. That way you're not guessing at what needs to be fixed. It's extra work upfront but saves you from potentially getting rejected again for the same or different issues.
I completely understand your frustration - ITIN rejections with vague explanations are unfortunately very common, especially for first-time applicants. The good news is that this is definitely fixable! A few immediate steps I'd recommend: 1. **Look for a rejection code** - Even though the letter seems vague, there's usually a small code (like "R 07" or similar) somewhere on the notice that indicates the specific issue. It might be in small print or in a corner. 2. **Call the ITIN hotline early** - Try 1-800-908-9982 right when they open at 8 AM. Yes, you'll likely wait 30-60 minutes, but it's much better than the impossible wait times later in the day. Have your rejection notice and original W-7 form ready. 3. **Double-check your treaty code** - Since you mentioned claiming treaty benefits, verify you selected the correct exemption code for your specific country and income type. The IRS has detailed treaty tables on their website that show exactly which codes apply to different situations. 4. **Consider a Certified Acceptance Agent** - They can review your documents in person and catch common issues before submission. Plus, you won't have to mail original documents. Don't give up! The treaty benefits you're entitled to are worth the extra effort to get this right. Most people succeed on their second attempt once they know exactly what needs to be corrected.
This is such great comprehensive advice! I'm dealing with a similar situation and had no idea about looking for those small rejection codes - I probably would have missed that completely. One quick question: when you mention the IRS treaty tables on their website, do you happen to know if they're updated regularly? I'm from Canada and want to make sure I'm using the most current treaty information when I resubmit. Also, has anyone had success with the online ITIN status tool, or is calling really the only reliable way to get specific details about what went wrong?
Daniel Rivera
Back in 2022, I had this exact same setup with Jackson Hewitt and the Serve card. I remember checking my card balance obsessively! One thing I learned from that experience is that the day of the week matters a lot. If the IRS releases your refund on a Friday, Jackson Hewitt often doesn't process it until Monday or Tuesday of the following week. Last year I filed on a Monday and got my refund exactly 14 days later on a Monday. The year before I filed on a Thursday and got it 16 days later on a Saturday. Since you filed on February 12th (a Monday), you might see it hit your card early next week.
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Camila Castillo
I used Jackson Hewitt with the Serve card this year and filed on February 5th. Got my advance immediately but didn't receive the remainder until February 22nd - so 17 days total. What's frustrating is that the IRS "Where's My Refund" tool showed my refund as sent on February 19th, but it took Jackson Hewitt 3 additional days to process and load it onto my Serve card. I think the delay you're experiencing might be normal this year. I noticed on Jackson Hewitt's website they mention that newly married couples filing jointly for the first time sometimes get additional IRS review, which could add 5-7 days. Since you mentioned this is your first year filing jointly after getting married, that could explain why it's taking longer than your single filing last year. Have you checked if your refund status changed on the IRS website recently?
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Emma Davis
ā¢@Camila Castillo That s'really helpful about the newly married filing jointly review! I didn t'know that was a thing. I ve'been checking WMR daily and it s'still showing Your "tax return is being processed -" hasn t'moved to refund "sent yet." Austin, since you mentioned you re'in the same boat with the newly married status, maybe that extra review period is what s'causing both of our delays compared to previous years. The 5-7 day extension Camila mentioned would put you right around where you should expect to see movement soon. Have you tried calling the IRS directly to see if there are any specific hold codes on your return?
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