I'm going through a similar situation right now and this thread has been incredibly helpful! I filed my SS8 back in October and I'm still waiting for the determination, but seeing everyone's success stories gives me hope. One thing I wanted to add for anyone else dealing with this - make sure you keep paying estimated taxes if you're still doing similar work elsewhere. I made the mistake of assuming my SS8 filing meant I could stop making quarterly payments, but that only applies to the specific employer relationship you're disputing. Also, has anyone dealt with the situation where you worked for multiple companies during the same tax year, but only one of them misclassified you? I'm trying to figure out how to handle the mixed W2/1099 situation when filing my amended returns if my determination comes back favorable. The documentation advice here is gold - I've been keeping everything in both digital and physical copies just to be safe. Better to over-document than under-document with the IRS! @Mateo Sanchez - definitely share this info with your former coworkers if you feel comfortable doing so. Worker misclassification often affects multiple people at the same company, and they deserve to know their rights. You could always just mention that you went through the SS8 process and let them research it themselves if they're interested.

Just wanted to jump in and say congratulations on your SS8 victory! As someone who's been helping people navigate tax issues for years, I can tell you that getting a favorable SS8 determination is no small feat - the IRS really scrutinizes these cases. A few additional tips based on what I've seen work well: 1. When you file Form 8919, consider requesting a paper check for your refund rather than direct deposit. Worker classification refunds sometimes get flagged in the electronic system, and paper checks tend to process more smoothly for these specific cases. 2. If you have any old email communications with your employer about work schedules, performance reviews, or company policies that applied to you, include copies with your amended returns. These really help establish the employer-employee relationship beyond what's already in your SS8 determination. 3. Keep a detailed log of your filing dates and confirmation numbers. With worker classification cases, it's not uncommon for the IRS to request additional documentation months later, and having everything tracked helps immensely. The fact that you were there for 18 months with clear control indicators (schedule, equipment, supervision) makes your case very strong. That $4,900 recovery estimate mentioned earlier sounds about right based on your self-employment tax amount. Best of luck with the process - you've already done the hardest part by getting that determination!

This conversation has been absolutely fantastic! As someone new to navigating private school expenses, I'm amazed by how many legitimate tax benefit options actually exist that I had no idea about. The 529 plan strategy for K-12 expenses is definitely my top priority to research now. The fact that you can contribute and withdraw almost immediately while still getting state tax benefits completely changes my perspective on these accounts. I always thought they were only worthwhile for long-term college planning. I'm also going to look into my state's specific education tax credits and programs. Reading about the Educational Improvement Tax Credit programs has opened my eyes to how much these benefits can vary by location - there might be opportunities right in my backyard that I've never heard of. One practical step I'm taking away is to contact my child's school about separating care costs from educational costs on their billing. Even small amounts that qualify for FSA treatment could add up to meaningful savings. The documentation advice throughout this thread has been invaluable too. It's clear that success with these programs depends on staying organized and understanding exactly which expenses qualify under which programs. I'm definitely going to start tracking everything systematically from now on. Thanks to everyone who shared their real experiences and specific examples. This community has provided more practical guidance than countless hours of trying to research tax code on my own!

This has been such an incredibly educational thread! I'm new to this community and in a very similar situation with my kids at a private academy. Reading through everyone's real-world experiences has been more helpful than anything I've found in my own research. What really strikes me is how many legitimate options actually exist that most families (myself included) never hear about. The 529 K-12 withdrawal strategy is definitely something I need to implement immediately - I had no idea you could contribute and withdraw almost instantly while still getting state tax deductions. I'm also fascinated by how state-specific many of these benefits are. It really emphasizes the importance of researching what's available in your particular location rather than just assuming the federal limitations apply everywhere. The Educational Improvement Tax Credit programs some of you mentioned sound particularly worth investigating. One thing I'm taking away is the critical importance of organization and documentation. It seems like the families who successfully maximize these benefits are the ones who carefully track which expenses go under which programs and maintain detailed records. I'm definitely going to start being much more systematic about this. For anyone else just discovering these options like me - it's encouraging to know that many of these strategies can be implemented retroactively for the current tax year, so we don't have to wait until next year to start seeing some relief. Thanks to everyone who shared their experiences and specific examples. This community is invaluable for navigating these complex financial decisions!

Great question about LLC classification elections! I've dealt with similar situations and wanted to add a few practical considerations. For your first scenario, while Connor's advice about the 75-day limitation is correct, there's actually another option worth considering. Since you haven't filed any returns yet and have an extension in place, you might want to explore whether your situation qualifies for "late election relief" under Rev. Proc. 2009-41. This allows retroactive elections up to 3 years and 75 days from the desired effective date if you can show reasonable cause. Given that all partners are voluntarily relinquishing their interests and you're dealing with a loss situation, you might have a strong reasonable cause argument. The key is including a detailed explanation with Form 8832 about why the election is late and why it's reasonable under the circumstances. One more thing to watch out for: if you go the deemed liquidation route that CosmicCowboy mentioned, make sure to properly handle any Section 754 election considerations if there are any inside/outside basis differences, though with an $8K loss this probably isn't relevant. For your second scenario, Emma's point about updating the operating agreement is crucial - the IRS will look at the substance of the arrangement, not just the form, so proper documentation is essential.

For the reasonable cause statement under Rev. Proc. 2009-41, you'll want to be very specific about the circumstances. In your case, I'd focus on: (1) the unanimous agreement of all partners to transfer their interests to one member, (2) the fact that only one member actually contributed to basis or participated in operations, (3) the administrative burden and cost of filing partnership returns when there's effectively only one economic owner, and (4) the fact that no returns have been filed yet, so there's no inconsistent reporting. Include documentation like the partnership agreement amendments showing the interest transfers, written consents from all partners, and any evidence that the other partners never actually contributed capital or participated in operations. Regarding Section 754 - even with a loss, if there's any difference between the inside basis of partnership assets and the outside basis of the departing partners' interests, a 754 election could be relevant. But in your situation with partners who never contributed to basis, this is probably not a concern. For the partnership validation in your second scenario, beyond the operating agreement, maintain records of: capital contribution documentation (bank records, property transfer docs), meeting minutes showing partnership decisions, separate partnership bank accounts, and any contracts or agreements signed in the partnership name. The IRS wants to see that you're actually operating as a partnership, not just calling it one on paper.

Benjamin, I feel your pain on this one! I went through something similar with my consulting business a few years back. The 5-year waiting period is brutal, but you do have some legitimate options beyond just waiting it out. Based on what you've described, I'd focus on the "reasonable cause" exception that others have mentioned. The fact that you revoked the S election when your business income was minimal ($40k) and you had a full-time job suggests you made a reasonable business decision at the time - not a tax avoidance scheme. Now that your circumstances have completely changed (full-time business, $180k projected income), you have a strong case for demonstrating that the original revocation wasn't primarily for tax benefits. The IRS has approved similar requests when taxpayers can show genuine business reasons. I'd recommend documenting everything: your income levels in 2023, your employment status change, projections for this year, and any advice you received that led to the original revocation. This paper trail will be crucial for your letter ruling request. The private letter ruling route isn't cheap (around $3,000-$7,000 in fees), but with your projected income level, the S corp tax savings would likely justify the cost. Just make sure you work with someone experienced in these types of requests - the formatting and arguments matter a lot. Don't give up! The IRS rejection letter is just their standard response, but exceptions do exist for situations like yours.

Benjamin, I've been following this thread and wanted to add another perspective based on my experience with S corp elections. You mentioned you've been relying on "random internet advice" - that's actually more common than you think, and it might work in your favor for the reasonable cause exception. The IRS recognizes that small business owners often make decisions based on general guidance available at the time. What matters is that you made a rational business decision given your circumstances (part-time business, minimal income, full-time employment). One thing I haven't seen mentioned yet is the timing of your quarterly estimated payments. Since you're projecting $180k this year and currently operating as an LLC, you're facing self-employment tax on the full amount. That's roughly $25k+ in SE tax alone that S corp status could help reduce significantly. Given the urgency of your tax situation, I'd actually recommend pursuing multiple approaches simultaneously: 1. File for the private letter ruling as others suggested 2. Consider the new entity approach (with proper legal structure to avoid substance-over-form issues) 3. Document everything about your 2023 decision-making process while it's still fresh The cost of professional help now is likely far less than the tax consequences of staying in LLC status for another 2+ years. Don't let the initial rejection discourage you - the IRS form letters rarely tell the whole story about available options.

I wanted to share my experience from last tax season since I was in a very similar situation. My partner and I received state cash assistance for about 8 months in 2023, and I was equally confused about the documentation requirements. After calling both the IRS helpline and our state's assistance office, I can confirm what others have mentioned - TANF benefits are indeed non-taxable and you won't receive a 1099-G for them. What really helped me was keeping a simple folder throughout the year with any correspondence from the state assistance program, even though none of it ended up being tax-relevant. It gave me peace of mind during filing season to be able to double-check that nothing in those documents indicated taxable income. Also, since you mentioned this is your first joint filing, don't forget to update your direct deposit information if you're expecting a refund - learned that lesson the hard way when our refund got delayed because we hadn't updated our banking details after marriage!

As a fellow newcomer to the tax world, I really appreciate this thread! Reading through everyone's experiences has been so educational. I'm in a similar situation where I received some state assistance last year and was worried about missing required documentation. It's reassuring to learn that TANF benefits don't generate tax forms and aren't considered taxable income. The analogy about it being like a gift from family really helped it click for me. I've bookmarked the IRS Interactive Tax Assistant tool mentioned earlier - seems like a great resource to have on hand. Thanks to everyone who shared their experiences and expertise here!