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Have you guys considered alternating years for who claims your son? My bf and I do this with our daughter - I claim her on odd years and he claims her on even years. Our accountant suggested this as the fairest approach since we both contribute similar amounts to her expenses.
I think that only works if the tax benefits are roughly equal for both parents. In my case, my income is way higher than my partner's, so I get a much bigger tax benefit from claiming our kid. We calculated it out and I save about $2,300 by claiming him while she would only save about $1,100, so I claim him and then just give her half the difference.
Good point about comparing the actual tax benefit! We never actually calculated out the difference - we just assumed it would be similar. Maybe we should run the numbers for this year and see if our alternating approach still makes sense or if we should do something more like what you described.
This is really helpful information everyone! I'm starting to see that the insurance split isn't the main issue - it's more about who provides the majority of support and how we can optimize our tax situation. @Paolo Longo - The Head of Household point is really important. I hadn't considered that aspect at all. Since I pay the mortgage and most utilities while my son's father covers groceries and some other expenses, I think I probably do pay more than half of the household costs. Combined with claiming our son as a dependent, that could mean significant tax savings with the HoH status. @Oliver Becker - Your approach of calculating the actual tax benefit difference and then sharing it makes a lot of sense. That seems much more fair than just alternating years without knowing the real impact. I think my next step is to sit down with my son's father and actually calculate out all our expenses and see who benefits more from claiming our son. The insurance coverage split should work fine as long as we're clear on the dependent claim. Thanks everyone!
That sounds like a really solid plan! One thing that might help with the calculations is keeping detailed records throughout 2025 of who pays for what. Since you're living together, it can get blurry sometimes about who covered which expenses, especially if you're sharing costs informally. Maybe consider setting up a shared spreadsheet or using an app to track household expenses as you go? That way when tax time comes around, you'll have clear documentation of the support percentages instead of trying to reconstruct everything from memory and receipts. It'll make the dependent claim decision much more straightforward and give you confidence that you're following the rules correctly.
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Has anyone had luck deducting part of their cell phone bill for delivery work? I use my phone constantly for the apps, GPS, customer communication etc.
Absolutely! I deduct 80% of my phone bill since I'm on the delivery apps all day. As long as you can reasonably estimate what percentage is used for business, you can deduct that portion.
Great question! Yes, you definitely should be tracking your mileage for 1099 delivery work - it's one of the biggest deductions you can take. Here's what I recommend: **For odometer readings:** You don't need to record it for every single trip, but do take photos of your odometer at the beginning and end of each work day, plus at the start/end of each year. This gives you solid documentation. **What to track for each delivery:** - Date and time - Starting point and destination - Miles driven (business purpose) - Total miles for the day **Pro tip:** Stop estimating immediately! The IRS can be strict about mileage deductions, and estimates won't hold up in an audit. Either use a mileage tracking app (like Stride, Everlance, or MileIQ) or keep a simple log in your car. You can choose between the standard mileage rate (67¢/mile for 2024) or actual vehicle expenses - the standard rate is usually better for delivery drivers and much simpler to track. Since you just started last month, you can still go back and reconstruct your mileage using your delivery app records, bank statements, and any receipts you have. Better to get organized now than scramble at tax time!
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Has anyone actually formed their LLC structure this way, with one disregarded LLC owning another? I'm curious how you handled the paperwork. When filing articles of organization for the second LLC, do you list the first LLC as the member, or do you still list yourself?
I did this last year. For the articles of organization, I listed my first LLC as the member/owner of the second LLC. But on my tax return, both businesses' income ended up on my personal 1040 (separate Schedule Cs). Just make sure all your organizational documents clearly show the ownership structure.
This is a great discussion! I've been considering a similar structure for my photography business and a separate e-commerce venture. One thing I wanted to add that hasn't been mentioned yet - make sure you keep meticulous separate records for each LLC even though they're both disregarded entities. The IRS may disregard them for tax purposes, but if you ever face an audit or legal challenge, you'll want crystal clear documentation showing that these are truly separate business activities. Keep separate bank accounts, separate bookkeeping, separate contracts - treat them as completely independent businesses operationally even if they're connected ownership-wise. Also, consider whether you might want to elect S-Corp status for either LLC down the road as your businesses grow. Having the separate entity structure already in place gives you more flexibility for tax planning in the future without having to restructure everything.
This is excellent advice about record keeping! I'm actually in a similar boat - just starting to explore this structure for my consulting business and a potential retail venture. The point about S-Corp election flexibility is something I hadn't considered. Quick question - when you mention keeping separate bank accounts, do you mean the first LLC should have its own account, and then the second LLC (owned by the first) should also have its own separate account? Or would it be acceptable for the first LLC's account to handle transactions for both since it owns the second? I'm trying to understand the practical day-to-day banking logistics of this setup before I commit to the structure.
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Has anyone used any particular tax software that handles aircraft leasebacks well? I tried TurboTax last year and it was clueless about how to handle my Cirrus SR22 leaseback situation. I ended up with a mess of misclassified items.
I've found TaxAct's business version handles it reasonably well, but you still need to know what you're doing. The key is selecting the right business code (532400) and then manually entering all the right expense categories. No consumer software really "understands" aviation businesses specifically.
I've been through this exact situation with my Cherokee Six on leaseback! A few additional points that might help with your tight deadline: For your Schedule C, make sure you're tracking your business miles separately from personal flying hours. The IRS distinguishes between transportation to/from the aircraft for business purposes versus recreational flying. Keep a detailed logbook. Since you mentioned you're doing maintenance work through the club at $0 labor rate, document this arrangement very carefully. Consider having the club issue you a 1099 for the fair market value of your services, then you can deduct that same amount as a business expense for maintenance. This creates a clear paper trail that the IRS can follow. One thing that saved me during an audit - keep detailed records of every communication with the flying club about scheduling, maintenance, and financial arrangements. Email chains, work orders, flight schedules, all of it. The IRS wants to see that this is a genuine business relationship, not just cost-sharing among pilot friends. Also, don't panic about filing something "reasonably accurate" now and amending later. As long as you're making a good faith effort with the information you have, you won't face penalties. The amended return route is actually pretty common for complex aviation businesses.
This is incredibly helpful advice, especially about the detailed documentation! I'm curious about the 1099 approach for the $0 labor rate maintenance work - wouldn't that create a wash situation where I'm reporting income and then deducting the same amount? Does the IRS actually prefer this approach over just documenting the arrangement as part of the leaseback agreement? Also, you mentioned keeping records of communications with the flying club. Should I be documenting my maintenance hours differently when I'm working on my own aircraft versus other club planes? I want to make sure I'm clearly separating business activities from what could be seen as personal aircraft ownership costs. With only 2 days left to file, I'm trying to prioritize which documentation is absolutely critical versus what I can clean up for the amended return later.
NebulaNomad
18 Does anyone know if this applies the same way for S corporations? I know S corps don't technically have E&P unless they were previously C corps, but I'm dealing with a converted entity that has accumulated E&P from its C corp days and did a §1031 exchange post-conversion.
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NebulaNomad
•11 For an S corporation that was previously a C corporation, the rules get a bit more complex. The accumulated E&P from the C corporation period stays with the company even after S election. If the S corporation does a §1031 exchange, and the property involved was held during the C corporation period, then any deferred gain would not have increased the C corporation's E&P at that time. When the replacement property is eventually sold, any gain attributable to the period when the company was a C corporation would potentially increase the accumulated E&P. It's super important to maintain good records in these situations because you need to track the portions of any gain attributable to appreciation during the C corp period versus the S corp period.
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Omar Zaki
This is a great discussion! I've been dealing with similar E&P confusion in my practice. One thing that helped me understand the §1031/E&P interaction was realizing that Congress intended E&P to reflect the corporation's actual economic capacity to make distributions to shareholders. Since a §1031 exchange doesn't generate any cash or other liquid assets (you're just swapping one property for another), there's no actual increase in the corporation's ability to pay dividends. The deferred gain represents potential future value, but not current distributable earnings. This is different from other types of gains that do increase current E&P because those transactions typically result in cash or other assets that could theoretically be distributed. The §1031 exchange keeps the corporation's economic position essentially unchanged from a liquidity standpoint, which is why E&P treatment follows the tax deferral rather than the book accounting recognition. I found Reg. §1.312-7 particularly helpful in understanding the specific E&P adjustments required for various types of property transactions if anyone wants to dive deeper into the regulations.
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