I can definitely relate to your stress about this situation! When I first saw a similar effective date issue on my own Form 2553, I thought my accountant had made a major error too. But after diving deep into the IRS regulations, I learned this is actually a well-established practice. The key thing to understand is that Revenue Procedure 2013-30 specifically addresses this exact scenario. When a corporation is formed during a tax year and wants S-Corp treatment, the IRS allows the election to be effective from January 1st of that year, even though the corporation didn't legally exist until later. This is purely a tax designation - your corporation's legal existence still begins on your incorporation date of June 5th. What makes this approach beneficial is that it gives you clean, consistent S-Corp tax treatment for the entire 2024 tax year. Without this, you might need to deal with more complex filing requirements for the period before incorporation. The "late filing" concern you mentioned is also addressed by this same revenue procedure. When newly-formed corporations make this type of retroactive election, the IRS automatically considers there to be reasonable cause for filing beyond the normal 2-month+15-day window. That said, I'd strongly recommend confirming with your accountant that they plan to include the proper explanatory statement with your first 1120-S filing. This documentation helps ensure the IRS understands the basis for the election timing. Most experienced tax professionals know to include this, but it's worth verifying since clear documentation protects you if any questions arise later. You're not in trouble here - this is actually a smart tax strategy that's used routinely for new S-Corps!

I went through almost the exact same situation with my S-Corp election about 6 months ago, and I completely understand your panic! When I first saw that January 1st effective date on my Form 2553 for a corporation I didn't even form until September, I was convinced my accountant had completely botched everything. But after all the research and stress, it turns out this is actually a very common and legitimate approach. What your accountant did falls under Revenue Procedure 2013-30, which specifically allows newly-formed corporations to elect S-Corp status retroactively to the beginning of the tax year. The IRS created this procedure exactly for situations like yours. Here's what I learned: the January 1st effective date doesn't mean your corporation somehow existed before June 5th. Your corp still legally exists only from its incorporation date forward. The retroactive effective date is purely for tax purposes - it just means your S-Corp election applies to the entire 2024 tax year once your corporation actually exists. The biggest benefit is simplicity - you'll only file one type of tax return (1120-S) for 2024 instead of having to deal with multiple entity types and filings for different parts of the year. The "late filing" issue you're worried about is also covered automatically - when newly-formed corporations make this type of election, the IRS considers it to have reasonable cause for being filed after the normal deadline. My advice: definitely talk to your accountant to understand their reasoning, but also ask them to confirm they'll include the proper explanatory statement with your first 1120-S return. That documentation is important to have on file in case the IRS ever has questions about the timing. You're not in trouble - this is actually smart tax planning that happens thousands of times every year!

I went through this exact same situation last year with a similar income level and two kids. Here's what I learned after consulting with a tax professional: At your income level ($235k), you're actually still below the child tax credit phase-out threshold for married filing jointly (which starts at $400k), so you should get the full $2,000 credit per child. However, the issue isn't really about claiming dependents vs not claiming them - it's about getting your total withholding right. What worked for us: We completed the W-4 accurately including our dependents in Step 3, but then added an extra $200 per paycheck on line 4(c) as additional withholding. This gave us a small buffer without massively over-withholding. The key insight is that the standard withholding tables sometimes don't perfectly account for all the interactions between income levels, deductions, and credits. Rather than playing games with the dependent section, it's better to be accurate there and then adjust with the additional withholding amount. One more tip: If you've been owing "several thousand" in recent years, look at your prior year tax returns to see what your actual tax liability was, then calculate if your current withholding will cover it. That's the most reliable way to avoid surprises.

This is a really common issue for higher-income families! I went through something similar when I started my current job. One thing that helped me was understanding that the W-4 is essentially your estimate of what your tax situation will look like for the year. Given that you've been owing several thousand dollars recently, it sounds like your withholding has been consistently too low. This could be due to various factors - maybe you have investment income, itemized deductions that are different from the standard deduction, or other complexities that the standard withholding tables don't capture perfectly. My recommendation would be to complete the W-4 accurately (including your dependents in Step 3 since you do qualify for the child tax credits), but then be conservative and add some extra withholding on line 4(c). Maybe start with an extra $150-200 per paycheck and see how that works out. The advantage of this approach is that you're not completely over-withholding like you would by claiming zero dependents, but you're building in a buffer to avoid that stressful tax-time surprise. You can always adjust it next year based on how this year turns out. Also, keep in mind that if your spouse works too, you'll need to coordinate the withholding between both of your jobs, which can get tricky. The IRS withholding estimator can help with that calculation.

Another thing to consider is that since you're earning substantial income from findom, you might want to look into forming an LLC for liability protection and potential tax benefits. While it's not required for filing taxes, an LLC can help separate your personal assets from your business activities and might provide some additional legitimacy if you're ever questioned about the nature of your business. Also, I'd strongly recommend getting professional liability insurance if you decide to treat this as a serious business. Some insurers offer coverage specifically for online service providers. It's relatively inexpensive and can protect you if any legal issues arise from your business activities. One more practical tip - start using a business calendar or scheduling app to track your work hours and client interactions. The IRS likes to see that you're operating like a real business, and having documented business activities can help support your Schedule C filing. Plus it helps you track which expenses are truly business-related vs personal. Finally, consider setting up a simple bookkeeping system now rather than scrambling next tax season. Even something basic like QuickBooks Self-Employed or a detailed Excel spreadsheet can save you tons of headaches later. The key is consistency - record everything as it happens rather than trying to reconstruct months of transactions later.

I really appreciate everyone sharing their experiences here! As someone who's been doing bookkeeping for small businesses for years, I can confirm that findom income definitely needs to be reported as self-employment income on Schedule C. One thing I'd emphasize that hasn't been fully covered is documentation strategy. Since payment apps don't always provide the best records for tax purposes, I recommend creating a simple monthly summary sheet that includes: date received, amount, payment method, and client identifier (doesn't have to be real names, just consistent codes like "Client A", "Client B"). This makes it much easier to cross-reference with your bank statements and payment app records. Also, regarding business expenses - don't forget about things like phone accessories (ring lights, tripods), any software subscriptions you use for editing or communication, and even a portion of your rent if you have a dedicated space you use exclusively for this work (home office deduction). Just make sure you can justify the business purpose for everything you deduct. The quarterly payment advice is spot on. Since you're past the January 15th deadline for Q4 2023, focus on getting your 2023 taxes filed correctly and start making estimated payments for 2024. The Form 1040ES has worksheets that help you calculate the right amount based on your expected income.

Has anyone successfully argued that a triple-net lease is actually a "business activity" rather than a "rental activity" for §469 purposes? I read somewhere that when the landlord has minimal services provided (as in a NNN lease), it's harder to argue it's not a rental activity subject to the passive loss limitations.

Great discussion here! One thing I'd add is to be very careful about the timing of your grouping election. As Andre mentioned, this generally needs to be done on your original return for the first year you're engaged in both activities. If you've already filed returns treating these as separate activities, it may be too late to group them unless you can demonstrate a material change in circumstances. Also, regarding the cost segregation study - while it can create significant depreciation deductions, make sure you're considering the potential depreciation recapture implications down the road if you ever sell the property. The accelerated depreciation from cost seg will be subject to recapture at ordinary income rates up to 25%. For documentation purposes, I'd recommend keeping detailed records of: 1) The business necessity of the rental property for your S-Corp operations, 2) Fair market rent analysis to support your rental rates, 3) Time records if you're trying to qualify as a real estate professional, and 4) Evidence of the integrated nature of the two activities. The IRS tends to scrutinize self-rental arrangements pretty closely, so having solid documentation will be crucial.

Has anyone actually had their return rejected specifically because of a printed scanned signature? I'm curious because I've done the print-sign-scan approach for 3 years now (living in Australia) and never had an issue. The IRS cashed my check and processed my return just fine each time.

I can confirm from personal experience that the scanned signature approach works perfectly fine. I've been filing from the UK for the past 4 years using exactly the method you described - sign the forms here, scan them, email to family in the US who print and mail them in. Never had a single issue with acceptance or processing. The IRS has been quite accommodating about this, especially as more Americans live abroad. Just make sure your signature is dark and clear when you scan it, and that it's positioned exactly on the signature line. One small tip: I always include a brief cover letter explaining that I'm filing from overseas, which seems to help the processing go smoothly. Also double-check that your parents include all pages in the correct order when they mail it - that's usually where mistakes happen, not with the signature itself.