Dumb question maybe, but what exactly happens if the statute of limitations runs out while they're still auditing? Does the whole thing just go away magically, or can they still assess taxes based on what they found up to that point?

Based on your situation, I'd actually recommend signing the Form 872 with a negotiated timeframe. Here's why: since you've already provided all documentation and are planning to accept their findings anyway, giving them adequate time to complete a thorough review could work in your favor. When auditors feel rushed by an expiring statute, they often make conservative estimates that lean heavily toward the government's position. With more time, they might catch calculation errors in your favor or give more consideration to borderline deductions. Since you mentioned the proposed increase is $4,200, I'd suggest signing the extension but negotiating it down to 6 months instead of the typical 1-year extension. This gives them sufficient time while still keeping some urgency to wrap things up. You can literally cross out the date on Form 872 and write in your preferred end date - most examiners will accept reasonable modifications. The key is being proactive about it. Contact your examiner and say something like: "I'm willing to sign the extension to give you adequate time to complete a thorough review, but I'd prefer to limit it to 6 months to bring closure to this matter." This shows cooperation while maintaining some control over the timeline.

One thing to consider - if you filed amended returns through a CPA, there may have been a substantial change in your reported income or deductions that triggered additional scrutiny. The certified mail could be related to that. I had this happen with my 2018 taxes when my CPA found significant deductions I'd missed. The IRS sent certified mail requesting documentation to verify those deductions. It wasn't an audit exactly, but they wanted proof before accepting all the changes.

Don't panic! Certified mail from the IRS is concerning but not necessarily catastrophic. The future date you're seeing (12/16 when today is 12/5) is actually normal - their system generates transcript entries before the physical notice is mailed. Given that this relates to your 2019 amended return and shows a $12,350 liability, this is most likely a CP2000 notice or similar correspondence about adjustments they've made based on your amendment. The $90 is probably a small penalty or interest charge. Here's what I'd recommend: First, don't stress too much until you actually receive and read the letter. Second, have all your 2019 tax documents ready along with anything your CPA filed for the amendment. Third, contact your CPA immediately when you get the letter since they're familiar with your situation. Most importantly, whatever the letter says, there are almost always options - payment plans, penalty abatements for first-time issues, or the ability to dispute if there are errors. The key is responding within the timeframe they give you (usually 30-90 days depending on the type of notice).

Don't forget about state requirements! The federal tax treatment as a disregarded entity doesn't necessarily mean your state treats it the same way. Here in California, even single-member LLCs have to pay an $800 annual tax regardless of profit, plus an LLC fee based on gross receipts if over $250,000.

Your cousin is definitely on the right track worrying about deadlines, but she can breathe a little easier! As a single-member LLC, she's considered a "disregarded entity" by the IRS, which means no Form 1065 needed - just Schedule C with her personal return by the April deadline. Even without profit, filing Schedule C is still important because she can deduct business expenses and potentially carry forward any losses to offset future income. Make sure she keeps detailed records of all business expenses like office supplies, equipment, business meals, etc. One thing to watch out for - while federal filing is straightforward with Schedule C, each state has its own LLC requirements. Some states require annual reports or have minimum taxes regardless of profit level. She should check her state's Secretary of State website to make sure she's not missing any state-specific deadlines or filings.

Has anyone considered the psychology of this? Even if it doesn't make financial sense (which everyone seems to agree it doesn't), there might be other valid reasons to quit a job. Mental health, family time, pursuing a passion, etc. Maybe reframe the question? If you really want to leave your job, perhaps focus on building that online selling business FIRST while still employed, then transition once it's generating enough income? Tax savings alone won't justify quitting, but if there are other benefits to you personally, those might tip the scales. Just something to consider.

I've been in a similar situation with multiple income streams, and I want to echo what others have said - the math almost never works out in favor of quitting for tax reasons alone. However, I'd suggest looking at some specific strategies that might help your situation without giving up that $115k: 1. Max out both your 401(k) contributions if your employers offer them - that's potentially $46,000 in pre-tax savings for 2024 ($23,000 each) 2. If either job offers HSA options, those are triple tax-advantaged 3. For your part-time work, make sure you're tracking ALL legitimate business expenses - home office, equipment, supplies, etc. The burnout you're experiencing is real and valid, but there might be other solutions. Could you negotiate remote work, flexible hours, or even a sabbatical at one of the jobs? Sometimes employers are willing to work with valuable employees to prevent turnover. If you do decide to build an online business, definitely start it as a side project first while keeping your current income. Once it's generating consistent revenue, then you can make an informed decision about transitioning away from traditional employment. Your financial security is worth more than the tax savings you'd get from a lower income bracket.

This is exactly the kind of comprehensive advice I was hoping for! Thank you everyone for sharing your experiences - both the successes and the costly mistakes. The recapture liability issue that Ethan mentioned is particularly eye-opening and definitely something I need to discuss with my attorney before moving forward. Based on what I'm reading here, it sounds like I have a few viable paths: specialized brokers like the ones Omar mentioned, platforms like taxr.ai that several people had success with, or checking if my state has an official exchange program. I'm leaning toward trying the platform approach first since the verification process seems like it could catch issues I might not be aware of. One follow-up question - for those who used brokers or platforms, did you get multiple offers to compare, or did you typically just go with the first reasonable offer? I want to make sure I'm not leaving money on the table, but I also don't want to drag out the process if the differences are minimal.

One thing I haven't seen mentioned yet is the timing aspect of transferable tax credit sales. Many people don't realize that the IRS has specific deadlines for when transfers must be completed and reported, and these vary by credit type. For example, with renewable energy credits, you generally need to complete the transfer by the end of the tax year in which the project was placed in service. Miss that deadline and you could lose the transferability entirely. Historic rehabilitation credits have different timing rules, and some state credits have even shorter windows. I learned this the hard way when I almost missed the deadline for transferring solar investment tax credits from a project we completed in December. Had to rush through the process and probably left money on the table because I didn't have time to properly shop around for buyers. My advice: start the process early, even if you're not ready to sell immediately. At minimum, get your documentation in order and understand your specific deadlines. Having everything ready allows you to move quickly when you find the right buyer or when market conditions are favorable.