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Ask the community...

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Aisha Khan

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5 Don't forget about self-employment tax! Since this is independent contractor work, you'll owe an additional 15.3% on top of your regular income tax for Social Security and Medicare. At six figures, this is going to be a significant amount. I'd recommend putting aside at least 30-35% of your income for taxes going forward. Also, you should definitely start making quarterly estimated tax payments this year to avoid underpayment penalties. The due dates are April 15, June 15, September 15, and January 15 of the following year.

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Aisha Khan

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15 Is there any way to reduce that self-employment tax? That's a huge chunk of money on top of regular taxes!

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Aisha Khan

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5 You can reduce your self-employment tax by forming an S-Corporation instead of operating as a sole proprietor. With an S-Corp, you pay yourself a reasonable salary (which is still subject to self-employment tax) but can take the rest of your profits as distributions that aren't subject to SE tax. However, there are additional costs and complexities with an S-Corp, including payroll processing, separate tax returns, and other compliance requirements. Generally, it's not worth considering until you're consistently making at least $80-100K in profit. Given your income level, it might be worth consulting with a tax professional who specializes in small businesses to see if this strategy would benefit you.

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Aisha Khan

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19 Does anyone know what happens if I just don't report some of this income? Like I got a 1099 from one platform but most of my income is just direct payments that aren't tracked that way.

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Aisha Khan

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8 BAD idea. The IRS has been cracking down hard on unreported income, especially from payment apps. As of 2022, platforms like CashApp, Venmo, PayPal etc. are required to report transactions to the IRS if they total over $600 in a year. Even if you don't get a form, they're sending the info to the IRS. Plus, if you have large deposits going into your bank account that don't match your reported income, that's a major audit flag. The penalties for intentional underreporting can include up to 75% of the unpaid tax plus interest, and potentially criminal charges for tax evasion. Not worth the risk with six-figure income!

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Don't forget that even if your vacation rental qualifies as non-passive, you still need to watch out for the At-Risk Rules and Excess Business Loss limitations. These can limit how much of your losses you can deduct in a given year regardless of the passive/non-passive classification. I learned this the hard way last year when I thought I could deduct my entire $45k short-term rental loss, only to find out the Excess Business Loss rules limited my deduction to a much smaller amount. Just something to keep in mind as you work through this.

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Natalie Chen

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Thanks for mentioning this! What exactly are the Excess Business Loss limits for 2025? I've been so focused on the passive vs non-passive issue that I totally overlooked this potential limitation.

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For 2025, the Excess Business Loss limitation is $300,000 for single filers and $600,000 for joint filers. This means if your total business losses exceed your business income by more than these thresholds, the excess gets carried forward to future years. For most people with a single vacation rental property, this limit isn't an issue. But if you have multiple properties or other business losses, it could come into play. The At-Risk Rules are potentially more relevant in your case - they limit your deductible losses to the amount you have "at risk" in the activity, which typically includes your cash investment, the portion of loans you're personally liable for, and certain qualified non-recourse financing.

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Am i the only one who thinks its absurd that something this important isn't clearly spelled out in Pub 527?? Like why do we have to piece together info from random regulations and forums to figure this stuff out?

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Ruby Garcia

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Totally agree! I feel like half of tax law is hidden in obscure regulations that normal people would never find. It seems like they make it intentionally complicated.

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Don't forget about state taxes too! Depending on where you live, you might need to pay state income tax on your photo sales. Some states also have business license requirements even for small operations.

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Omg I totally didn't even think about state taxes! I'm in California - do you know if they have any special requirements for small online businesses?

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California definitely has state income tax, and they're pretty thorough about collecting it! You'll need to report your income on your CA state tax return. California also technically requires a business license for most businesses, though many small online sellers operate without one initially. If your sales exceed $600 annually, you should register for a Seller's Permit with the California Department of Tax and Fee Administration, especially if you're selling any physical products alongside your digital content. For purely digital goods like photos, the rules can be a bit different, but it's still income that needs to be reported.

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Sunny Wang

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Can I just say that the term "side hustle" needs to die? The corporations have tricked us into thinking we need multiple jobs to survive and then glamorized it with cute names. In the 70s one job could support a family but now we're all out here selling feet pics just to make rent šŸ˜’

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This is actually helpful tax advice for OP's question though? Maybe save the economic commentary for another thread.

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Ella Russell

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Quick question - do S-Corps still get the 20% pass-through deduction (QBI) like sole props do? I heard something about income limits and wasn't sure if S-Corps have different rules for that.

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Yes, S-Corps are eligible for the 20% Qualified Business Income deduction. The same income thresholds apply ($170,050 for single filers and $340,100 for joint filers in 2025). Above those thresholds, limitations based on W-2 wages and qualified property start to phase in. Actually, this is where S-Corps can have an advantage over sole props for high earners. Since you're paying yourself a W-2 salary, that can help you qualify for larger QBI deductions if you're over the income threshold. It's a bit complicated but basically your W-2 wages to yourself can help satisfy the wage limitation tests.

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Gavin King

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S-Corps are awesome but no one talks about how the IRS scrutinizes them more. My friend got audited specifically because he took too much in distributions compared to salary. They reclassified a bunch of his distributions as wages retroactively and he owed a ton in back taxes + penalties. Make sure your salary vs distribution split can pass the smell test!

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Don't forget to check if you qualify for the Qualified Business Income Deduction (QBI) with your Schedule C businesses! That's a potential 20% deduction on your qualified business income. That might explain why the tax website is showing you owe so much - if you didn't account for that deduction.

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Aisha Khan

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Thank you for mentioning QBI! I didn't even know about that deduction. Do both of my businesses qualify for that? And would I apply it to each Schedule C separately?

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Yes, both of your businesses should qualify for the QBI deduction as they're both reported on Schedule C. The deduction is actually calculated on your total qualified business income across all qualifying businesses, not on each Schedule C separately. The basic calculation is 20% of your net business income (after expenses), but there are income thresholds where it starts to phase out or get more complicated (over $170,700 for single filers in 2024, which doesn't sound like it applies to you). This deduction alone could significantly reduce what you owe, possibly explaining the high amount you saw on the first website you tried.

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GalacticGuru

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When I had two Schedule Cs, I found it helpful to use tax software specifically designed for self-employed people rather than the free options. The extra $50-60 was worth it for the guidance on splitting expenses and proper documentation.

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Which tax software did you use? I tried [popular tax software] and it didn't explain anything about allocating home office expenses between multiple businesses.

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