For your wife's nanny income, wouldn't she need to pay self-employment tax too? That's an extra 15.3% on top of regular income tax, right? That seems like it would be a big hit on back taxes you're already struggling with.

Just wanted to add my perspective as someone who went through a similar situation with back taxes and missing documentation. The advice about reporting the nanny income as "other income" on Schedule 1 is spot on - that's exactly what I did when I had unreported cash payments from years ago. One thing that really helped me was creating a simple spreadsheet showing how I estimated the income. I listed things like "worked approximately 20 hours/week from March-December 2018 at $15/hour" with whatever details I could remember. Even if it's not perfect, the IRS appreciates seeing that you made a good faith effort to be accurate. Also, don't stress too much about the payment plan approval. In my experience, the IRS is pretty reasonable about setting up installment agreements, especially when you're proactively trying to get caught up. The fact that you've already filed 2019-2023 shows you're making an effort to stay compliant going forward. Filing jointly is almost certainly going to be better than separately - you'll get a higher standard deduction and potentially qualify for credits you'd lose filing separately. Just get that 2018 return filed with your best estimate and move forward with getting current.

Congratulations on your new baby! Your situation is totally manageable. Since you completed your OIC in 2021, you're well within the 5-year compliance period, but that doesn't prevent you from setting up payment plans for new tax debts. The key thing is to act promptly - file your 2023 return on time (or request an extension) and set up the payment plan before the payment deadline. This actually helps demonstrate compliance with your OIC terms rather than hurting it. Given that you're on short-term disability with a newborn, I'd strongly recommend being conservative with your monthly payment amount. With a $9,500 balance, you could set up a plan for as low as $130-140/month and still pay it off within the IRS's 72-month maximum timeframe. You can always increase payments later when you're back to full income. The online payment agreement tool is probably your best bet for quick setup. Just keep in mind the current interest rate is around 8% annually, so if you have low-interest alternatives available, it might be worth comparing the total cost.

I'm in a very similar situation - had an OIC accepted in 2019 and now dealing with new tax debt while on reduced income. What really helped me was understanding that the IRS actually prefers you to proactively set up a payment plan rather than just letting the debt sit there. One thing I learned the hard way is to make sure you communicate with the IRS about your situation. When I called to set up my payment plan, I mentioned that I had a previous OIC and was currently on reduced income due to medical reasons. The representative noted this in my file and actually suggested a lower monthly payment than I had initially requested. Also, since you're on short-term disability, you might qualify for Currently Not Collectible (CNC) status if your financial situation is truly dire. But given that you have some savings and just want to preserve your emergency fund with a new baby, the payment plan sounds like the smarter approach. The peace of mind is worth it - especially when you're already dealing with the stress of a newborn and recovery from childbirth. You're being responsible by addressing this promptly rather than ignoring it.

Has anyone successfully gotten their broker to reverse the backup withholding? I'm in a similar situation (wrong middle initial) and just noticed nearly $3500 was withheld from a stock sale last month. My broker is saying they can't do anything about it now that the money has been sent to the IRS.

I went through a very similar situation a few years ago when my brokerage had an outdated SSN on file (long story involving a name change). The backup withholding hit me on a large mutual fund redemption and I was panicked about whether the IRS actually received the money. Here's what I learned: The IRS systems are notoriously slow to update, so don't expect to see backup withholding reflected in your online account immediately. Your brokerage is required to send the withheld funds to the IRS within a specific timeframe, and they have strong incentives to comply since they face penalties if they don't. For verification, I found the most reliable approach was to keep detailed records of the withholding from your brokerage statements and wait for your 1099 forms. The 1099-B (for stock sales) will show both your proceeds and the backup withholding amount. This is your official documentation that the IRS will accept. Regarding quarterly payments - you're absolutely right that you can adjust them. The IRS cares about your total tax payments for the year, not the timing or method. If your backup withholding exceeds your projected liability, you can reduce or skip estimated payments accordingly. Just make sure to run the numbers carefully to avoid underpayment penalties.

Have you considered reaching out to the Volunteer Income Tax Assistance (VITA) program? They offer free tax preparation services for people with disabilities, and many locations now provide remote options due to COVID adaptations they've maintained. While they don't offer advances directly, they might be able to expedite your filing to get your refund faster. Do you qualify for any special credits related to your disability that might increase your refund amount? What's your timeline for needing the funds?

I'm really sorry to hear about your Credit Karma situation - that's incredibly frustrating, especially when you're dealing with disability challenges and counting on that advance! 😔 Based on what others have shared, here are a few solid options to consider: **Quick alternatives with advances:** • H&R Block online - seems to have good disability accommodations and 24-48 hour processing • TaxSlayer - another user just got approved for $1,250 in 37 hours • Jackson Hewitt online - also offers refund advances **Things to watch out for:** • Fees can range $25-100, so compare the total cost • Some advances are smaller than advertised • New platforms have learning curves **Alternative approach:** Some folks found that filing with faster services like FreeTaxUSA or TaxAct without an advance actually got their refund in 8-12 days, which wasn't much slower than advances anyway and saved on fees. Given your disability needs, I'd probably start by checking H&R Block's online platform since multiple people mentioned their good accessibility features. Whatever you choose, make sure to read all the fee disclosures carefully before committing. Hang in there - there are definitely workable solutions for your situation! 💪

This is exactly the situation I went through 2 years ago! We started as an LLC with 3 co-founders and converted to a Delaware C-Corp when we were ready for our seed round. A few things I learned that might help: 1. The LLC structure was perfect for our first 18 months - we could deduct startup losses on our personal returns and had maximum flexibility with profit/loss allocations between founders. 2. When we converted, we used what's called a "statutory conversion" rather than having the C-Corp acquire the LLC. This was cleaner from a tax perspective and avoided some of the complications others mentioned. 3. One unexpected benefit of starting as LLC first: it forced us to really think through our partnership dynamics and operating agreements early on. When we converted to C-Corp, we had a much clearer sense of roles, equity splits, and governance than friends who started directly as corporations. 4. Timing-wise, we started the conversion process about 4 months before we wanted to close our seed round. This gave us plenty of time to get everything sorted without feeling rushed. The key is having good legal and tax counsel when you're ready to make the switch. Don't try to DIY the conversion - there are too many ways it can go wrong and create expensive problems later.

I've been through this exact transition and can confirm it's a solid strategy when done right. We started as an LLC for the tax benefits and simplicity, then converted to a Delaware C-Corp about 6 months before our Series A. A few additional considerations that haven't been mentioned yet: 1. **State considerations matter** - If you're planning to operate in multiple states, starting as an LLC can actually be more complex than a C-Corp due to varying state LLC laws. Delaware C-Corps have much more standardized treatment across states. 2. **Employee equity complications** - If you plan to hire employees early and offer equity compensation, LLCs make this much more complex. LLC membership interests don't qualify for things like ISOs (Incentive Stock Options), so you'll likely end up using profit interests or other structures that are harder for employees to understand. 3. **Banking and vendor relationships** - Some banks and enterprise customers prefer working with corporations over LLCs for perceived stability and standardization. That said, the tax pass-through benefits in early loss years can be substantial. We saved about $15k in the first year alone by being able to deduct startup losses on our personal returns. My advice: if you're bootstrapping and expect to be unprofitable for 12+ months, start as LLC. If you're planning to raise money within the first year or hire employees immediately, consider starting as a C-Corp to avoid the conversion complexity later.