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Leslie Parker

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This is a really common confusion for gig workers! The key thing to remember is that when you choose the standard mileage deduction, you're essentially trading off the ability to claim vehicle depreciation or losses for the simplicity of just tracking miles. The IRS considers that depreciation component already "built into" those standard mileage deductions you've been taking over the past 3 years. Since you mentioned keeping good records of business vs personal miles, that's great practice to continue! Even though you can't claim the loss on this sale, those records will be valuable if you get audited or when you start using your next vehicle for business purposes. One thing to keep in mind - if you do replace this car with another vehicle for your delivery work, you'll need to decide again between standard mileage or actual expenses for the new car. Just remember that whichever method you choose in the first year of business use for that new vehicle, you'll be locked into for the life of that car.

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This is super helpful, thanks! I'm actually in a similar boat - been doing Uber Eats for about 2 years with standard mileage and my car is starting to cost more to maintain than it's worth. Quick follow-up question: when you say we're "locked into" the method for the life of the car, does that apply to brand new cars too? Like if I buy a completely different car next month, can I choose actual expenses for that one even though I used standard mileage on this current car?

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Daniel Rogers

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Yes, exactly! The method you choose is locked in per vehicle, not per taxpayer. So when you get a completely different car, you get a fresh choice between standard mileage or actual expenses for that new vehicle, regardless of what method you used on your previous car. Just make sure to keep the decision consistent for that new vehicle once you make it. If you choose standard mileage in the first year you use the new car for business, you'll need to stick with standard mileage for as long as you use that specific car for business purposes. Same goes if you choose actual expenses - you'd be committed to tracking all the actual costs (gas, maintenance, insurance, depreciation) for that vehicle's business use. This is actually a good opportunity to evaluate which method might work better for your situation with the new car!

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Xan Dae

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I went through this exact same situation last year with my delivery car! Used standard mileage for 2+ years, then sold at a loss. I was so frustrated thinking I was missing out on a tax deduction, but after doing a lot of research (and talking to a tax pro), I learned that the standard mileage rate actually works out pretty well overall when you factor in all the wear and tear costs it covers. Think about it this way - over those 3 years of deliveries, you've been deducting around 65+ cents per business mile (the rates have gone up each year). That adds up to thousands in deductions that already account for your car's depreciation. While you can't claim the loss now, you've likely saved more in taxes over the years through those mileage deductions than you would have with the actual expense method. For your next car, definitely consider whether actual expenses might work better if you expect to put a lot of business miles on it quickly. But honestly, for most delivery drivers, standard mileage is still the simpler and often more beneficial choice!

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Tyrone Johnson

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That's a really good point about the math working out over time! I never thought about adding up all those mileage deductions over the years. You're probably right that it comes out ahead in the long run. I'm curious though - for someone just starting out with gig work, is there a rule of thumb for deciding between standard mileage vs actual expenses? Like if you expect to drive more than X miles per year, go with actual expenses?

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5 Has anyone tried MyExpatTaxes? Their website claims to specialize in US taxes for expats, but I can't find many reviews from actual users.

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11 I used MyExpatTaxes last year while in Germany. It was pretty decent - definitely designed for expats and handled Form 1116 and Form 2555 well. The interface is simpler than TurboTax but has all the expat-specific features. Cost me about $149 for federal, which isn't cheap but less than an accountant. They also have good expat-specific support if you get stuck.

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NeonNova

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I've been filing as an expat in Canada for the past 4 years and wanted to share my experience with FreeTaxUSA. While it's not specifically marketed for expats, it actually handles Form 1116 and Form 2555 quite well once you upgrade to their Deluxe version ($14.99). The interface isn't as polished as some of the other services mentioned, but it gets the job done for straightforward expat situations. I particularly like that they don't try to upsell you constantly like some other platforms do. However, fair warning - their customer support isn't great if you run into complex international tax questions, so you'll need to do your homework beforehand. One thing I learned the hard way: make sure whatever service you choose can handle amended returns easily. I had to file a 1040X my second year abroad to correct a mistake with my foreign tax credit calculation, and FreeTaxUSA made that process relatively painless.

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Yara Sabbagh

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Thanks for mentioning FreeTaxUSA! I hadn't considered them since they don't really advertise to expats. Quick question - did you run into any issues with foreign address validation? That's been my main problem with some of the cheaper services. Also, when you filed the 1040X, were you able to do it through their platform or did you have to mail it in manually?

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Yuki Kobayashi

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Based on everyone's responses here, it sounds like you're definitely on the right track - you don't need to check the multiple jobs box since you're only working one job currently. One thing I'd add is that if you're worried about your withholding being accurate (especially with the salary increase from $62k to $71k), you might want to run the IRS withholding calculator in a few months once you have a couple paystubs from your new job. That way you can see if you need to adjust anything for the rest of 2025. Also, keep in mind that having that gap between jobs might actually work in your favor tax-wise since your total 2024 income was probably lower than it would have been if you'd worked the full year at either salary level.

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Maya Lewis

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That's a really good point about the income gap potentially working in your favor! I hadn't thought about that angle. Since you were unemployed for a few months, your total 2024 income was definitely lower than a full year at either job would have been. Just wanted to add - when you do run that IRS withholding calculator that others mentioned, make sure you have your final paystub from your old job handy so you can enter the exact amounts that were already withheld. That'll give you the most accurate picture of whether you need to adjust anything going forward.

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LilMama23

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Great question! I went through something similar when I switched jobs last year. Everyone here is absolutely right - that multiple jobs checkbox is only for when you're working more than one job at the same time, not for sequential employment like your situation. Since you're only working one job now, you can skip that entire section. The W4 is all about setting up proper withholding going forward from your current employer, not accounting for what happened earlier in the year. One tip though - since your new job pays more ($71k vs $62k), you might want to check the IRS withholding estimator in a month or two once you have a few paystubs. The higher salary could put you in a different tax situation, and it's better to catch any underwithholding early rather than owe a big chunk next April! But for now, just fill out the W4 as if this is your only job (because it is), and you should be all set.

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Kaitlyn Jenkins

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This is such helpful advice! I'm actually in a similar boat - just started a new job after being laid off earlier this year, and I was stressing about the W4 form. It's reassuring to hear from someone who went through the same thing. Quick question though - when you mention checking the IRS withholding estimator in a month or two, do you enter info from both your old job AND your new job for 2024? Or just focus on the new job since that's what's affecting your 2025 withholding? I want to make sure I'm doing this right!

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Understanding Tax Consequences When Distribution is Treated as Sale of Shareholder's Stock and Corporation Recognizes Loss in Liquidation

I'm struggling with a corporate tax question about liquidation and would appreciate some help understanding the answer. The scenario involves a corporation (Zenith Inc) that's being liquidated. Brad owns 40% and Rachel owns 60%. They started the company 7 years ago, and Brad's current basis in his shares is $125k. When they liquidate Zenith, Brad receives property (Greenfield) that the corporation bought 4 years ago worth $780k with a basis of $600k. Rachel receives property (Yellowfield) worth $1.2M with a basis of $1.5M. Rachel had contributed this property in a Section 351 exchange 7 years ago. At that time, Rachel's basis in Yellowfield was $1.5M and its FMV was $1.3M. The question asks about tax consequences to Rachel and Zenith, with these options: a. Distribution to Rachel treated as dividend if Zenith has enough E&P b. Distribution to Rachel treated as redemption under ยง 302(b)(2) c. Distribution treated as sale of Rachel's stock; Zenith won't recognize gain/loss d. Distribution treated as sale of Rachel's stock; Zenith recognizes $300k loss e. Distribution treated as sale of Rachel's stock; Zenith recognizes $100k loss I thought the answer was (c) but apparently it's (d) and I'm not understanding why. Can anyone explain why Zenith would recognize a loss in this situation? I thought distributions in liquidation were generally tax-free to the corporation.

Jamal Carter

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This has been an excellent deep dive into corporate liquidation tax rules! As someone who handles corporate restructuring, I see these Section 336 issues frequently and this discussion really captures the key nuances. One additional point that might be helpful: when advising clients on liquidations, it's important to consider the timing strategically. If Zenith had significant E&P and wanted to avoid the loss recognition (perhaps due to limitations on loss utilization), they could have considered distributing the loss property in a non-liquidating distribution first (where Section 311 would disallow the loss), followed by a later liquidation of remaining assets. Of course, that strategy has its own complications and may not achieve the shareholders' business objectives, but it illustrates how the choice between liquidating vs. non-liquidating distributions can have dramatically different tax consequences for the corporation. The explanations here about Section 336's "deemed sale" treatment and the 5-year anti-abuse rules under 336(d)(2) are spot-on. This is exactly the kind of technical analysis that helps distinguish between seemingly similar answer choices on these corporate tax problems. Really appreciate everyone's contributions!

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Mason Stone

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That's a really insightful strategic point about timing distributions! I hadn't considered how corporations might use non-liquidating distributions first to avoid loss recognition under Section 311, then follow with liquidation of remaining assets. It really highlights how the sequencing of transactions can dramatically impact tax outcomes. Your example makes me think about how important it is to consider the overall tax picture, not just the mechanical application of the rules. If Zenith had NOL limitations or other factors that made the $300k loss less valuable, the Section 311 strategy could make sense even with the additional complexity. This discussion has really opened my eyes to how nuanced corporate tax planning can be. What started as a question about why answer (d) was correct has evolved into a comprehensive analysis of liquidation rules, anti-abuse provisions, and strategic considerations. As someone relatively new to corporate tax, I'm grateful for all the practical insights shared here!

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Harper Collins

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This thread has been absolutely invaluable for understanding corporate liquidation tax rules! As a CPA working with small corporations, I encounter these Section 336 vs Section 311 issues regularly, and the explanations here have really clarified some concepts I've been struggling with. What I found most helpful was the step-by-step breakdown of why this is treated as a "deemed sale" under Section 336 rather than a regular distribution under Section 311. The key insight that complete liquidations have their own special tax regime really clicked for me. I've been making the mistake of trying to apply regular distribution rules to liquidation scenarios. The discussion about the 5-year rule under Section 336(d)(2) was particularly enlightening. I had a similar case last year where property was contributed 3 years before liquidation, and now I understand why only part of the loss was recognized. The built-in loss limitation makes so much sense from a policy perspective. For other practitioners dealing with these issues, I'd recommend always documenting the contribution dates and built-in gains/losses at the time of contribution. It's crucial for determining how much loss the corporation can actually recognize in a subsequent liquidation. Thanks to everyone who contributed - this has been one of the most educational threads I've seen on corporate tax!

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Megan D'Acosta

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For business gifts, I'd strongly recommend avoiding cash or personal checks entirely - they're almost impossible to properly document and will likely raise red flags if audited. The IRS wants clear evidence that this was a business expense, not personal spending. A few solid alternatives that work well: - Visa gift cards are actually fine IF you keep excellent records (receipt, business purpose note, proof of delivery) - Branded promotional items that prominently display your logo can potentially qualify as marketing expenses beyond the $25 limit - Gift baskets with a mix of branded and non-branded items (document the branded portion separately) The key is documentation. Whatever you choose, make sure you have: (1) receipt showing purchase, (2) written note explaining the business relationship and purpose, and (3) proof it was actually given to the client. I keep a simple spreadsheet tracking all client gifts with photos of receipts attached. Remember that even if you spend more than $25, you can only deduct $25 per person per year for true gifts. But legitimate promotional/marketing expenses with clear business purpose may qualify for full deduction if properly documented.

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Yuki Ito

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This is really helpful advice! I'm curious about the documentation requirements - when you say "proof it was actually given to the client," what kind of proof works best? Is a simple email saying "thanks for the gift" sufficient, or do you need something more formal like a signed receipt? I'm planning my first client appreciation gifts and want to make sure I have everything properly documented from the start.

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Chloe Taylor

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Great question! For proof of delivery, I've found that email acknowledgments work well - either a "thank you" reply from the client or even just your own email to them saying something like "Hope you enjoy the gift basket I sent over." Photos can be helpful too - I sometimes take a quick photo when hand-delivering or keep the shipping confirmation if mailing. The IRS isn't looking for formal signed receipts, just reasonable evidence that the expense was legitimate and business-related. I also include the client's business relationship in my notes (e.g., "referral source who sent 3 new clients in 2024" or "longtime client celebrating 5-year partnership"). This helps establish the business purpose if questioned. One tip: if you're hand-delivering, send a follow-up email mentioning it. Something simple like "It was great seeing you today - hope you enjoy the coffee gift set!" This creates a paper trail that's easy to reference later.

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Amara Oluwaseyi

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Just to add another perspective on this - I've found that timing can be really important with client gifts. If you're giving a gift immediately after landing a new client or receiving a referral, it's much easier to document the clear business purpose. But if you wait months or give gifts randomly without a specific business event, it becomes harder to justify as a legitimate business expense. I typically give gifts within 30 days of a referral or major milestone, and I always include a handwritten note that specifically mentions the business reason (e.g., "Thank you for referring Smith Industries - looking forward to working with them!"). This creates a clear paper trail linking the gift to a specific business purpose. Also worth noting that if you're planning to do this regularly, consider setting up a simple system from the start. I use a basic spreadsheet with columns for date, client name, gift description, amount, business purpose, and receipt location. Makes tax time much easier and shows the IRS you're treating this seriously as a business expense rather than just random personal gifts.

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Mei Zhang

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This is excellent advice about timing and documentation! I'm just starting my consulting business and was wondering - for someone who's completely new to client gifts, what would you recommend as a safe starting point? Should I stick strictly to the $25 limit until I better understand the rules, or is it worth exploring the promotional/marketing expense route from the beginning if I use branded items? I want to make a good impression on early clients but also don't want to mess up my taxes in my first year of business.

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