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?

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.

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.

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!

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 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.

I'm dealing with a very similar situation right now! Got my CP14 notice last week even though I've been faithfully making my monthly payments since February. It's such a relief to see I'm not the only one this has happened to. What really helped me was logging into my IRS online account like Jamal mentioned - it clearly showed my installment agreement was still active and all my payments were recorded. That gave me some peace of mind while I worked up the courage to call them. I finally got through yesterday using the early morning strategy (called at 7:15 AM EST) and the agent was actually really understanding. She confirmed that these notices are generated automatically and don't account for active payment plans. She put a note on my account to prevent any collection actions and said I should stop receiving the notices within 4-6 weeks. One thing she told me that I hadn't seen mentioned here - if you get any additional notices while this is being sorted out, there's a specific line on the CP14 that says something like "If you have an installment agreement, disregard this notice." It's in small print near the bottom, but it's there for exactly these situations. Keep making your payments and don't stress too much about it. The system is just slow to catch up!

This thread has been incredibly helpful! I'm actually going through this exact situation right now - got a CP14 notice yesterday despite having an active payment plan since March. Reading everyone's experiences has really calmed my nerves. I wanted to add one thing that might help others: when I set up my installment agreement, I took screenshots of every confirmation page and saved the PDF of the agreement itself. I also set up email notifications for each payment through my bank so I have a paper trail showing exactly when each payment was processed. The timing issue makes so much sense now that everyone's explained it. I was worried I'd done something wrong, but it sounds like this is just how their systems work (or don't work together). I'm going to try calling early tomorrow morning with all my documentation ready. For anyone else dealing with this - definitely keep making your payments like everyone said. I almost considered stopping them thinking my plan was canceled, which would have been a huge mistake. Thanks to everyone who shared their experiences, especially about the specific wording to use when calling!

Has anyone here successfully used a vehicle under 6,000 lbs for a business deduction recently? What documentation did you need during tax time? My tax guy is telling me one thing but what I'm reading online is different.

Great question! I've been dealing with this exact situation for my marketing consultancy. You're absolutely right that vehicles under 6,000 lbs can still qualify for business deductions - just not the full Section 179 treatment that the heavy trucks get. For your photography business with 80% business use, here's what I've learned: **Standard Mileage vs. Actual Expenses:** - Standard mileage is simpler (currently $0.67/mile for 2024, likely similar for 2025) - Actual expenses can be better if you have a pricier vehicle or high maintenance costs - You can't switch between methods once you choose for a specific vehicle **Key things for vehicles under 6,000 lbs:** - Annual depreciation limits apply (around $19,200 first year max, then lower amounts in subsequent years) - You'll depreciate over 5 years using MACRS - Keep detailed mileage logs from day one - this is crucial for audits **My recommendation:** Run the numbers both ways before deciding. For a reliable crossover/sedan with 80% business use, actual expenses often work better than mileage if you're buying new or newer used. Also, consider timing your purchase - if you buy late in the year, you might want to wait until January to maximize your first-year deduction under the half-year convention rules. Document everything religiously - the IRS scrutinizes vehicle deductions heavily!