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Ask the community...

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I'd definitely recommend starting with the IRS online transcript service at irs.gov/transcripts - it's usually the fastest option if you can get through their identity verification. As a small business owner myself, I know how hectic things can get and record-keeping sometimes falls by the wayside! If you filed electronically, there's also a chance your tax software provider (TurboTax, H&R Block, etc.) might still have a copy in your online account. Also worth checking if you emailed it to yourself or saved it in cloud storage. The transcript is usually sufficient for most purposes, but if you specifically need the actual 1040 form with all attachments, you'll need to use Form 4506 with the $43 fee. What do you need it for? That might help determine which option would work best for your situation.

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Emma Davis

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This is really helpful advice! I'm in a similar situation as a new small business owner and I'm already worried about keeping track of everything for next year's taxes. Do you have any recommendations for better record-keeping systems that work well for busy entrepreneurs? I don't want to end up in this same situation next year!

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I actually went through this exact same situation last year when I needed my 2022 return for a business loan application. Here's what worked for me: I started with the IRS online transcript service, but like others mentioned, the identity verification can be tricky. When that didn't work, I called my tax preparer first - they had a copy on file and were able to email it to me within hours. If you did your own taxes, check your email for any confirmations from tax software companies, as they often include a PDF copy. For future reference, I now save three copies: one in my email, one in Google Drive, and one printed copy in my filing cabinet. The transcript is usually fine for most business purposes, but some lenders specifically want the actual 1040 form. What do you need it for? That might help narrow down which option would be most efficient for your timeline.

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Just to add another perspective - make sure you're also considering state tax implications if applicable. Some states have different rules about bad debt deductions than federal, so what's deductible on your federal return might not be on your state return. Also, if you haven't already, I'd strongly recommend getting a tax professional involved given the amount you're dealing with ($14k is significant). They can help ensure you're maximizing your deductions while staying compliant, especially since this is your first time handling this situation. The cost of professional advice is usually worth it to avoid potential issues down the road. One last tip - keep a separate file for each bad debt with all your collection documentation (emails, call logs, letters, etc.). If you ever get audited, having everything organized by individual debt makes the process much smoother.

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Liv Park

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This is really solid advice, especially about state tax differences. I learned this the hard way when I moved my business from California to Texas - what I could deduct federally wasn't the same for state taxes. Also totally agree on getting professional help for $14k worth of deductions. That's definitely audit-worthy territory and having a CPA review everything upfront is way cheaper than dealing with problems later. Plus they might catch other deductions you're missing that could offset the consultation cost. The organized filing system is clutch too. I use a simple spreadsheet tracking each bad debt with columns for original invoice date, services provided, collection attempts made, and final determination date. Makes it super easy to pull everything together come tax time.

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Freya Collins

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Great discussion here! As someone who's dealt with similar issues, I want to emphasize the importance of establishing a clear written policy for bad debt write-offs before you actually need it. The IRS looks favorably on businesses that have consistent, documented procedures for determining when debts become uncollectible. I'd recommend creating a simple policy that outlines your collection process (initial invoice, follow-up at 30 days, final notice at 60 days, etc.) and when you'll consider a debt worthless (like after 120 days with no response despite documented attempts). Also, don't forget to check if your state requires you to attempt service of a formal demand letter before writing off debts over certain amounts. Some states have specific requirements that could affect your deduction eligibility. One more tip - if any of these customers are other businesses, you might want to check if they're still operating before writing off the debt. Sometimes a quick search of state business records can reveal if they've dissolved, which strengthens your case that the debt is truly uncollectible.

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This thread has been incredibly helpful! I'm dealing with the exact same situation with my 18-year-old who worked at Target last year. One additional tip I'd add: make sure your son keeps a copy of his filed return for his records, even though the amounts are small. When he applies for financial aid for college (FAFSA), they'll ask for his tax return information. Having filed his own return actually made the FAFSA process cleaner for us since his income was already properly documented. Also, if he plans to work again this year, this experience will make next year's filing much easier since he'll already understand the process. My daughter is now confident enough to handle her taxes independently after we walked through it together the first time. Thanks to everyone who shared their experiences - it's reassuring to know this is such a common and straightforward situation!

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Zara Mirza

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That's such a great point about the FAFSA connection! I hadn't thought about how filing his own return would help with college financial aid applications. My son is a senior this year and we'll definitely be dealing with FAFSA soon, so having his tax information properly filed separately makes a lot of sense. Thanks for mentioning that - it's one more reason to go ahead and have him file even though his income was relatively low.

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Sarah Jones

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This is such a timely question! I'm dealing with the same situation with my 17-year-old who will turn 18 next month and has been working at a local restaurant since last summer. From reading through all these responses, it sounds like the consensus is pretty clear: your son should definitely file his own return and check the "can be claimed as dependent" box. What I'm taking away from everyone's experiences is that this is actually a really common situation and the process is more straightforward than it initially seems. I especially appreciate the point about this being a good learning opportunity. My daughter went through this two years ago, and while I was nervous about "doing it wrong," it ended up being a great way for her to understand how taxes work before she becomes fully independent. One thing I'd add is to make sure you have all his tax documents ready before you start - W-2, any 1099s if applicable, and maybe print out the instructions for the "can be claimed as dependent" section so you can reference it while helping him file. Having everything organized upfront made the process much smoother for us. Thanks for asking this question - it's helping me feel more confident about handling this with my son when the time comes!

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The Boss

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This is such a complex situation with so many variables! I went through something similar with a rental property donation two years ago. One thing I learned that might help - consider getting multiple appraisals if you're going the direct donation route. The IRS can be very picky about property valuations, especially for high-value donations like yours. Also, timing matters a lot. If you're planning to donate in December, make sure you have all your documentation ready well in advance. The charity needs time to process the donation and provide you with the proper acknowledgment forms before year-end. Another consideration - some charities have minimum property value requirements or geographic restrictions. I found that land conservancies and some religious organizations were more willing to accept real estate donations than smaller local charities. Given the complexity and the dollar amounts involved, I'd strongly recommend getting professional advice from both a tax attorney and a CPA who specializes in charitable giving. The depreciation recapture rules alone are tricky enough that you want to make sure you're calculating everything correctly.

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TommyKapitz

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One strategy that hasn't been mentioned yet is using a Charitable Remainder Trust (CRT) if you're looking to spread out the tax benefits and potentially avoid some of the depreciation recapture. With a CRT, you transfer the property to the trust, which then sells it and pays you an income stream for a specified period or your lifetime. You get an immediate charitable deduction for the present value of the remainder interest that will eventually go to charity. The key advantage is that the trust can sell the property without you personally recognizing the capital gains or depreciation recapture - those taxes are deferred and spread out over the payment period. However, CRTs are complex and expensive to set up, so they typically only make sense for higher-value properties or if you want the income stream feature. Another option to consider is a Charitable Lead Trust if you're more focused on estate planning benefits, though that's probably overkill for your situation. Given your numbers ($390K FMV, $130K depreciation), you're right at the threshold where these more sophisticated strategies might be worth exploring. I'd definitely recommend running the numbers on a CRT scenario before making your final decision.

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Rita Jacobs

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This is really helpful information about CRTs! I'm curious about the income stream aspect - how is that income taxed? Is it treated as ordinary income, or does it retain the character of the underlying property (like capital gains)? And are there minimum distribution requirements like with retirement accounts? Also, you mentioned CRTs are expensive to set up - what kind of costs are we talking about? Legal fees, trustee fees, ongoing administration? Trying to figure out if the tax benefits would outweigh the setup and maintenance costs for a $390K property.

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I'm a bit late to this conversation but wanted to add that understanding this hierarchy is super important for actual tax planning! My accountant saved me thousands last year by relying on a Tax Court decision that contradicted an IRS publication. He explained that court decisions outrank IRS publications in the hierarchy, so we were on solid ground taking the position. The IRS initially questioned it during review, but once we cited the relevant Tax Court case, they accepted our position. Just shows why knowing which authorities take precedence matters in real-world situations!

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Do you remember which Tax Court case it was? I might be in a similar situation and would love to look it up!

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This is such a great question and the responses here are really helpful! As someone who struggled with this concept in my tax law course, I'd add that it's crucial to remember that the hierarchy can get complicated in practice. One thing that helped me was understanding that while the Internal Revenue Code is the primary statutory authority, Treasury Regulations come in two types: interpretive regulations (which explain existing law) and legislative regulations (which Congress specifically authorized the Treasury to create). Legislative regulations carry almost as much weight as the IRC itself. Also, don't forget about the practical side - even though court decisions are lower in the hierarchy than the IRC and regulations, if there's a recent Supreme Court or Circuit Court decision that interprets a tax provision differently than an old regulation, practitioners will often follow the court decision until the Treasury updates the regulation. The key is understanding not just the theoretical hierarchy, but how it works when sources conflict with each other in real situations!

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StarSailor

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This is exactly the kind of practical insight I needed! I've been so focused on memorizing the theoretical hierarchy that I never thought about how it works when sources actually conflict. The distinction between interpretive and legislative regulations is something my textbook barely touched on but seems really important. Your point about practitioners following recent court decisions over outdated regulations makes total sense - it's like the hierarchy becomes more fluid in real practice. Do you have any tips for identifying whether a regulation is interpretive vs legislative when you're researching? That seems like it would make a big difference in determining how much weight to give it.

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