My company uses a strategy where we have a separate LLC that owns the aircraft and then leases it back to the main business for specific business trips. This creates clearer documentation for business use vs personal use. The management company can also charter the aircraft to other businesses when we're not using it, which helps offset costs and creates a clearer business purpose.

One thing I haven't seen mentioned yet is the importance of having a written aircraft use policy if you're serious about this. The IRS loves to see documented policies that clearly define what constitutes business use vs personal use for company aircraft. Your policy should specify things like: who can authorize flights, what documentation is required for each trip, how to handle family members or guests on business flights, and what happens if plans change mid-trip (like extending a business trip for personal reasons). I've seen businesses get in trouble during audits not because their use was inappropriate, but because they couldn't demonstrate they had clear policies and consistently followed them. The IRS views this as evidence that the company takes the business purpose requirement seriously rather than just using the aircraft as a personal convenience. Also consider that some states have different rules for sales/use tax on aircraft, which can be significant on such a large purchase. Make sure you're considering the full tax picture, not just federal income tax deductions.

I've been dealing with this exact same situation! As someone who manages several short-term rentals, I initially made the same mistake of issuing 1099-NECs instead of 1099-MISCs. The confusion is totally understandable because we think of property management as providing a service, but the key is what the payment represents. When you're distributing rental income that belongs to the property owners, you're not paying them for services - you're returning their rental income. This should go on 1099-MISC Box 1 (Rents), not 1099-NEC. The difference is huge for the recipients because 1099-NEC income gets hit with self-employment tax (15.3%) while rental income on Schedule E typically doesn't. To answer your question about correcting the forms - yes, you can void the 1099-NEC and issue a corrected 1099-MISC. I had to do this last year for several owners. Just make sure you're still within the filing deadlines. Most of my owners were actually grateful when I corrected this because it saved them significant money on their taxes. It's definitely worth making the change going forward!

Great question about the correction process! When you void a 1099 form, you typically need to file a corrected version with "CORRECTED" checked on the new form rather than just voiding it. The IRS wants to see both the correction and what you're correcting it to. You'll submit the corrected 1099-MISC through the normal filing process (either electronically or by mail) and the system handles the rest. As for amended returns, several of my property owners did choose to file Form 1040X for the past three years to recover overpaid self-employment taxes. The savings were substantial - we're talking about potentially recovering 15.3% of all that rental income that was incorrectly reported as self-employment income. I provided them with a letter explaining the error and the corrected forms to support their amended filings. One tip: I created a simple spreadsheet showing each owner exactly how much they could potentially recover by filing amended returns for each year. This helped them decide if it was worth the effort. For most of them, the savings were in the thousands of dollars, so it was definitely worthwhile. The key is being proactive and transparent with your clients about the mistake and the opportunity to recover those overpaid taxes.

Just wanted to share my experience as someone who went through this exact situation last year. I was making around $600/month from similar online content and was terrified about filing taxes independently for the first time. The key things that helped me: 1. Set aside 25-30% of each payment for taxes (self-employment tax hits hard!) 2. Track EVERYTHING - I use a simple spreadsheet with date, amount, platform, and any expenses 3. Open a separate bank account just for this income - makes tracking so much easier 4. Consider making quarterly estimated tax payments if you're consistently earning over $400/month I ended up owing about $1,200 in taxes on $7,000 of income, but because I had been setting money aside, it wasn't a financial shock. The business expense deductions really do help - I was able to deduct my phone, internet, some clothing/accessories, and even a small portion of rent for my "home office" space. Don't let the fear of filing stop you from reporting everything properly. The IRS is surprisingly reasonable if you're honest and proactive, but they're ruthless if they catch you hiding income.

I know this might feel overwhelming since it's your first time handling taxes independently, but you're asking all the right questions! Here are the key points to remember: **Yes, you absolutely must report this income.** At $400-500/month, you're looking at $4,800-6,000 annually, which is well above any reporting thresholds. This income gets reported on Schedule C as self-employment income. **Don't worry about your mom seeing it.** You can file your own taxes completely independently. Use a generic business description like "Digital Marketing" or "Online Content Creation" - no need to be more specific. **Start preparing now:** - Open a separate bank account for this income if possible - Set aside 25-30% of each payment for taxes (you'll owe both income tax and self-employment tax) - Keep records of ALL payments received, even small ones - Save receipts for any business expenses (phone bill percentage, props, lighting, etc.) **Consider quarterly estimated payments** since you're earning consistently. This prevents a big tax bill next April. The good news is there are legitimate business deductions available to content creators that can significantly reduce your tax burden. Just make sure everything is properly documented. You've got this!

wait how do you even set up an IP PIN? asking for a friend lol

Just to add some reassurance - I work in tax prep and see this situation all the time. Once your return is "received" in the system, creating an IP PIN won't trigger any flags or cause processing delays. The IRS systems are separate - your 2024 return will continue processing normally while your new IP PIN gets set up for future use. You made a smart choice getting it set up proactively!

Different approach to consider - since the sale is definitely going to be counted in 2024 based on the closing date, you might want to look at other ways to offset that income to avoid the bracket jump. Do you have any investment losses you could harvest before year-end? Or could you make extra retirement contributions if you have any self-employment income? Maybe accelerate charitable donations you were planning for next year? Sometimes when you can't change when the income hits, you can still manage other aspects of your tax situation to mitigate the impact. Just a thought!

I went through almost the exact same situation two years ago - December 30th closing with funds arriving January 3rd. After consulting with my CPA and getting confirmation from the IRS, it's definitely based on the closing date, not when you receive the money. However, there are a few things that might help with your situation. First, make absolutely sure you're capturing ALL your selling expenses - realtor commissions, staging costs, legal fees, title insurance, any repairs you made specifically to prepare for sale, etc. These all reduce your taxable gain. Second, since you mentioned this was a rental for 5+ years, double-check your depreciation records. Sometimes people forget to claim depreciation in earlier years, and you'll be hit with depreciation recapture whether you claimed it or not. If you missed claiming depreciation you were entitled to, you might want to file amended returns for those years to get the benefit of the deductions. Also worth noting - if this pushes you into the higher bracket where the 3.8% Net Investment Income Tax kicks in, that's another layer to consider in your planning. The loss harvesting strategy mentioned above is smart if you have any losing positions. You could also look at accelerating other deductions into 2024 if possible. Good luck with the CPA consultation!