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!

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!

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.

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.

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!

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!

Something no one mentioned - if this is your first year as a sole proprietor, you technically qualify for a safe harbor based on last year's taxes. If you had zero tax liability last year, you may not need to make estimated payments your first year.

As a fellow sole proprietor who went through this same confusion, here's what I wish someone had told me clearly: You need to make quarterly PAYMENTS (not file returns) if you expect to owe $1,000 or more in taxes. The deadlines are April 15, June 15, September 15, and January 15. Your 20% savings rate might not be enough - I learned the hard way that you need to account for both regular income tax AND self-employment tax (15.3%). I typically set aside 25-30% to be safe. The easiest way to start is to use Form 1040-ES to calculate your first quarter payment, then you can just make payments online through IRS Direct Pay without mailing forms each time. Keep detailed records of all business income and expenses - you'll need them for your annual Schedule C filing. Don't stress too much about getting it perfect the first year. The IRS understands learning curves, and as long as you're making good faith efforts to pay what you owe, any small penalties are manageable. The key is to start now rather than wait!

This is such a helpful thread! I'm in a similar situation and was totally confused about the EIN requirements. Just to make sure I understand correctly: I can open a Solo 401k right now as a sole proprietor using my SSN, and then I'll need to get a separate EIN specifically for the retirement plan itself (not for my business). Is that right? Also, when you all mention "Form SS-4 for banking purposes" - is that different from the SS-4 you'd file when starting a new business? I want to make sure I'm checking the right boxes when I apply for the plan EIN. One more question - if I decide to form an LLC later for liability protection, would I need to transfer the Solo 401k to the LLC or can I keep it under my original sole proprietorship structure? Some of the comments mention it depends on how the LLC is taxed but I'm still a bit unclear on the details.

This thread has been incredibly helpful! I'm actually a tax preparer and see this confusion all the time with my self-employed clients. Just wanted to confirm what everyone's been saying and add a few practical tips: You absolutely CAN open a Solo 401k as a sole proprietor with just your SSN - I help clients do this regularly. The plan EIN is totally separate and you'll apply for it after opening the account. A few things to keep in mind: - Make sure you have legitimate self-employment income (1099s, business income, etc.) - The contribution deadline is your tax filing deadline (including extensions) - You can actually contribute for 2024 up until April 15, 2025 if you haven't already - Keep good records of your contributions for tax preparation One last tip: if you're making good money as a freelancer, definitely run the numbers on a Solo 401k vs SEP-IRA. The Solo 401k almost always wins for contribution limits, but the SEP-IRA can be simpler if you ever plan to hire employees. Most of my self-employed clients without employees go with the Solo 401k for the higher limits. Good luck with your retirement planning!