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4 Has anyone used TurboSelf-Employed for this situation? Is it good at handling both W-2 and Schedule C income?
23 I used it last year for my exact situation (full-time job + side hustle) and it worked well. It walks you through tracking quarterly payments and helped me understand what deductions I qualified for. Pretty user friendly.
One thing that helped me tremendously when I started my side business was using Form 1040ES worksheets to calculate my quarterly payments more precisely. The IRS provides these worksheets specifically to help people in situations like yours estimate what they owe. The key insight is that you don't need to worry about being pushed into higher tax brackets - tax brackets are marginal, meaning only the income above each threshold gets taxed at the higher rate. Your 40% set-aside is likely more than sufficient for most income levels. Also consider the safe harbor rule: if you pay either 100% of last year's tax liability (110% if your prior year AGI exceeded $150,000) OR 90% of this year's liability through withholding and estimated payments, you won't face penalties even if you owe a bit more at filing time. This gives you some breathing room while you figure out the right withholding amount.
This is really helpful, especially the part about the safe harbor rule! I had no idea about the 100%/110% of last year's tax liability option. That actually gives me a concrete target to aim for instead of just guessing. One follow-up question - when you mention Form 1040ES worksheets, do these account for the fact that I already have W-2 withholding happening? I want to make sure I'm not double-counting or over-paying through both my regular job withholding AND quarterly payments.
One additional strategy worth considering is implementing an Employee Stock Ownership Plan (ESOP) if your retail business has sufficient value and cash flow. While more complex than the other options discussed, ESOPs can provide massive tax deferrals and even permanent tax avoidance on the sale proceeds if structured properly. For a less complex approach, consider maximizing your HSA contributions if you're on a high-deductible health plan. For 2025, you can contribute $4,300 for individual coverage or $8,550 for family coverage (plus $1,000 catch-up if over 55). While the amounts aren't huge compared to retirement plans, every bit helps when you're in the phase-out range. Also, if you're doing any business travel or have a home office, make sure you're maximizing those deductions. The home office deduction can be particularly valuable for S-corp owners - you can either take the simplified method ($5 per square foot up to 300 sq ft) or actual expense method if you have significant home office costs. Finally, consider income shifting through family partnerships or gifting business interests to adult family members in lower tax brackets, though this requires careful structuring and ongoing compliance. The key is finding the right combination of strategies that work for your specific situation while staying well within IRS guidelines.
Thanks for mentioning the HSA option - that's one I completely overlooked! We do have a high-deductible health plan, so maxing out HSA contributions is definitely something we can implement immediately. Every thousand dollars helps when you're trying to stay below those phase-out thresholds. The ESOP suggestion is interesting but probably too complex for our situation right now. However, the home office deduction point is really valuable. I've been using the simplified method, but given our income level, it might be worth calculating the actual expense method to see if we can get a larger deduction. Do you happen to know if there are any special considerations for S-corp owners claiming home office deductions compared to sole proprietors? Also, regarding the family partnership idea - we don't have adult children yet, but I'm curious about the mechanics. Would this involve actually gifting ownership stakes in our retail business, or are you referring to creating separate partnership entities for certain business activities? The income shifting concept sounds promising for future planning as our kids get older.
For S-corp owners claiming home office deductions, there are a few key differences from sole proprietors. You'll typically claim the deduction on Form 8829 and then the business reimburses you for the home office expenses, rather than taking it directly on Schedule C like sole proprietors do. This creates a legitimate business expense for the S-corp while providing you with tax-free reimbursement. The actual expense method might indeed be better for you given your income level - especially if you have significant mortgage interest, property taxes, utilities, or depreciation that can be allocated to the business use percentage. Just make sure to keep detailed records and photos of your dedicated office space. Regarding family partnerships, there are actually several approaches. The most common for retail businesses is gifting minority interests in the S-corp itself to adult family members (though this requires careful valuation and gift tax planning). Alternatively, you could create separate LLCs for specific business activities (like real estate if you own your building) and gift interests in those entities. The key is ensuring any family members receiving income are actually providing legitimate services to justify the income shifting. Given your current situation with the QBI phase-out, I'd focus on the immediate strategies first - HSA maximization, home office optimization, and the retirement plan enhancements others mentioned. The family planning strategies are great for future years as your children reach adulthood.
Another approach that might help with your QBI situation is exploring captive insurance company strategies if your retail business has sufficient income and risk exposure. While more sophisticated than traditional retirement plans, captives can allow you to deduct up to $1.2 million annually in premiums while building tax-deferred wealth. For a simpler immediate strategy, consider accelerating any business loan payments or prepaying business expenses like insurance, rent, or supplier agreements if you have the cash flow. These prepayments can create legitimate business deductions in the current year while providing operational benefits. Also, don't overlook equipment leasing versus purchasing decisions. If you need new fixtures, POS systems, or delivery vehicles, structured leases might provide better current-year deductions compared to depreciation schedules, especially with the reduced bonus depreciation percentages for 2025. One often-missed opportunity: if your retail business involves any intellectual property (proprietary processes, customer lists, brand development), consider whether those assets should be held in separate entities and licensed back to your operating company. The licensing fees create deductions for the S-corp while potentially qualifying for different QBI treatment. The key is layering multiple strategies rather than relying on just one approach. Given that you're already maxing retirement contributions, combining several smaller strategies (HSA, home office optimization, expense timing, equipment decisions) can collectively move you back into the favorable QBI range.
Has anyone used QuickBooks Online for handling the accrual method with unshipped inventory? I'm struggling with the same issue as OP.
I use QBO with accrual and what worked for me was creating a liability account called "Customer Deposits" or "Deferred Revenue." Then when you receive payment before shipping, record it to that account instead of income. I use a Sales Receipt that points to the liability account rather than income.
I'm a newcomer here but dealing with a very similar situation! I've been researching the accrual method switch for weeks and this thread has been incredibly helpful. One thing I'm still confused about - when you're tracking inventory only at the beginning and end of the year (not quarterly), how do you handle COGS throughout the year? Do you estimate it based on purchases, or do you wait until year-end to make adjustments? Also, for those who mentioned Form 3115, is there a specific deadline for filing it when switching methods? I want to make sure I don't miss any important timing requirements. The deferred revenue approach makes total sense for unshipped orders. I'm definitely going to implement that in my QuickBooks setup. Thanks everyone for sharing your experiences!
Great thread with lots of helpful info! I wanted to add one important point about record-keeping that might help others in similar situations. Even if you've lost original receipts, the IRS accepts "reconstructed records" as long as they're reasonable and based on available evidence. I learned this when preparing for my home sale last year. You can use: - Bank statements showing payments to contractors or home improvement stores - Credit card statements with clear descriptions - Canceled checks made out to contractors - Permits pulled for work (these are public records) - Before/after photos with written explanations - Contractor invoices or estimates (even old ones) The key is being able to demonstrate that the improvements actually happened and provide a reasonable estimate of costs. I was able to reconstruct about $35,000 in improvements this way, which made a huge difference in my capital gains calculation. Also, don't forget about smaller improvements like new appliances, fixtures, or even landscaping that adds value - these all count toward your adjusted basis if you have documentation.
This is incredibly helpful! I never thought about using permits as documentation. My county has an online permit search system, so I just looked up my address and found records for my deck addition from 2018 and bathroom remodel from 2020. The permit applications actually show the estimated project costs, which should help establish a reasonable basis for those improvements. Thanks for mentioning this - it's going to save me a lot of stress about missing receipts!
One thing I haven't seen mentioned yet is the importance of documenting the selling expenses when you calculate your capital gains. These can significantly reduce your taxable gain and include: - Real estate agent commissions (usually 5-6% of sale price) - Title insurance and escrow fees - Attorney fees - Transfer taxes - Home inspection fees paid by seller - Staging costs - Marketing expenses - Any repairs required by the buyer as part of the sale These selling expenses are subtracted from your sale price along with your adjusted basis to determine your actual capital gain. For a $400,000 home sale, you might have $25,000+ in selling expenses, which is a substantial reduction in your taxable gain. Also, @AstroAlpha, regarding your mother's inheritance situation - make sure she gets a proper appraisal of the property's fair market value as of the date of death. This becomes her new basis, and having professional documentation will be crucial if the IRS ever questions the stepped-up basis amount. Don't rely on online estimates like Zillow - get a real appraisal from a licensed appraiser.
This is such valuable information about selling expenses! I had no idea that staging costs and marketing expenses could be deducted. When you mention "marketing expenses," does that include things like professional photography for the listing, or are we talking about more substantial advertising costs? Also, if I end up doing some quick repairs before listing (like touching up paint or fixing minor issues), would those count as selling expenses or would they be considered improvements to the basis?
Hugo Kass
Does anyone have experience with how this affects state returns? I'm in California and dealing with a similar situation. Would reclassifying from ordinary income to rental income on the federal flow through correctly to CA Form 565?
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Josef Tearle
ā¢For California, the reclassification should flow through since CA Form 565 generally follows federal characterization of income. However, California has its own passive activity rules that can sometimes differ from federal. One thing to watch for: California suspended NOL deductions during some recent tax years, so if your reclassification creates passive losses in prior years, check if those years were affected by the NOL suspension. Also, the self-employment tax savings won't have a direct state tax impact since CA doesn't have an equivalent to SE tax, but the income characterization will still matter for passive activity purposes.
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Oliver Brown
This is a great discussion on rental income classification. I want to add a practical tip that might help with documentation when you amend these returns. When I've dealt with similar partnership rental misclassifications, I always prepare a detailed memo explaining the correction that gets attached to the amended return. I include citations to IRC Section 1402(a)(1) which specifically excludes rental income from self-employment tax, and Reg. 1.1402(a)-4 which clarifies that real estate rentals are not considered carrying on a trade or business for SE tax purposes. For the self-rental aspect, I also cite Reg. 1.469-2(f)(6) to show that while the income may be recharacterized as non-passive under the self-rental rules, it's still rental real estate income exempt from SE tax. This documentation has been helpful when dealing with IRS inquiries on amended returns. One more thing to consider - if your clients have been overpaying SE tax for multiple years, make sure you calculate the interest the IRS will owe them on the refunds. For substantial amounts, that interest can add up to a meaningful sum that clients appreciate knowing about upfront.
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PixelPrincess
ā¢This is really helpful documentation advice! I'm new to dealing with partnership amendments and wondering - when you prepare these memos, do you typically file them as a rider to Form 1065X or include them as supporting documentation? Also, have you found that providing the regulatory citations upfront helps speed up IRS processing of the refund, or does it not make much difference in their review timeline? I'm dealing with a similar situation where my clients have been overpaying SE tax on rental income for three years, so the refund amount is pretty substantial. Any tips on how to present this to clients in a way that doesn't make them lose confidence in their previous preparer while still explaining the error?
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