I went through this exact decision process about 18 months ago when buying my home. After consulting with both my CPA and attorney, I decided against putting my primary residence in my LLC name, and I'm glad I did. The main factors that swayed me were: 1) Loss of the primary residence capital gains exclusion - this alone could cost you hundreds of thousands in taxes when you sell 2) Mortgage rates and terms are significantly worse for commercial/business property loans 3) The complexity of calculating fair market rent to yourself creates ongoing compliance headaches 4) Home office deduction works the same whether you own personally or through business One thing I did do was get an umbrella insurance policy instead, which gives me excellent liability protection for a fraction of the cost and complexity. For around $400/year, I have $2M in additional liability coverage that protects all my assets including my business. Unless you're in an extremely high-risk profession where you expect frequent lawsuits, the tax downsides of business ownership for a primary residence far outweigh any potential benefits. Save the LLC structure for actual investment properties where it makes more sense.

I appreciate everyone's detailed responses here - this has been incredibly enlightening! As someone who's been managing payroll taxes and business compliance for my LLC, I was definitely underestimating the complexity that business-owned residential property would add. The point about losing the capital gains exclusion really hit home. In my area, home values have appreciated significantly, so giving up that $250K exclusion could literally cost me six figures down the road. That alone makes this a non-starter. I'm also realizing that my initial assumption about "better tax write-offs" was probably based on outdated or incomplete information. If the home office deduction works the same either way, and I'd have to pay myself fair market rent (creating taxable income for the business), it sounds like I'd actually end up paying MORE in taxes, not less. Think I'll stick with personal ownership and look into that umbrella insurance approach that was mentioned. Getting better liability protection for $400/year versus creating a tax nightmare seems like a no-brainer. Thanks for saving me from what would have been a very expensive mistake! Sometimes the "clever" tax strategy isn't actually clever at all.

I'm dealing with something similar and appreciate everyone sharing their experiences here. The stress of wondering "what if" has been eating me alive for months. After reading through all these responses, it seems like the consensus is pretty clear - coming forward voluntarily is almost always better than waiting to get caught. The penalties are lower, you avoid potential criminal charges, and you can actually sleep at night again. I'm curious though - for those who amended their returns, how did you handle the payment? Did you pay everything upfront or were you able to set up payment plans? The amount I'd owe is more than I can pay immediately, so I'm wondering what options the IRS typically offers for people in our situation. Also, has anyone here actually been audited for unreported income? I keep seeing advice about audit triggers and red flags, but would love to hear from someone who actually went through the audit process to understand what that's really like.

I've been following this thread as someone who went through a similar situation a few years back. The advice here is solid - voluntary disclosure really is your best option. One thing I want to emphasize that hasn't been mentioned much: document EVERYTHING when you prepare your amended returns. Keep records of all your income sources, bank statements, and any evidence of the cash deposits. The IRS appreciates thoroughness when you're coming forward voluntarily. Also, don't underestimate the psychological toll this takes. I was a wreck for months before I finally amended my returns. The relief you feel after taking care of it properly is incredible - it's like a huge weight lifted off your shoulders. Your situation with the capital losses potentially triggering scrutiny is definitely valid. The IRS has algorithms that flag discrepancies between reported income and financial activity. Better to address it on your terms rather than theirs. One last tip: if you do decide to work with a tax professional, make sure they specialize in IRS issues and have experience with voluntary disclosures. Not all tax preparers are equipped to handle these situations properly.

Great question! You're absolutely right that donating appreciated securities directly to charity is one of the best tax strategies available. Just want to add a few practical tips from my experience: 1. Make sure to get a written acknowledgment from the charity that specifically states they received securities (not just cash), includes the date of transfer, and describes the securities donated. This is crucial for your tax records. 2. If you're donating a large amount, consider spreading it across multiple tax years to stay within the 30% AGI limitation for appreciated property donations. You can carry forward unused deductions for up to 5 years. 3. Consider donating your most highly appreciated shares first - the ones with the lowest cost basis give you the biggest tax benefit since you're avoiding the most capital gains tax. 4. Time the donation strategically if you're close to year-end. The deduction counts for the tax year when the charity receives the shares, not when you initiate the transfer. With your cost basis being only 30% of current value, you're looking at substantial tax savings. This strategy could save you thousands in capital gains taxes while maximizing your charitable impact!

This is exactly the situation I was in last year with some Berkshire Hathaway shares I'd held since 2005! The strategy worked perfectly - I donated shares worth about $50k with a cost basis of only $12k directly to my local food bank. A few things I learned that might help you: 1. Contact the charity first to make sure they can accept stock donations. Many smaller organizations aren't set up for this, but most established charities have procedures in place. 2. Your broker will need the charity's DTC number and account details. The charity should be able to provide this quickly if they're equipped to handle stock donations. 3. Keep detailed records of the transfer date, number of shares, and the stock price on that date. You'll need this for Form 8283 if your donation is over $500. 4. The fair market value is calculated as the average of the high and low trading prices on the date the charity receives the shares. In my case, I avoided about $5,700 in capital gains taxes (15% on the $38k gain) and got to deduct the full $50k market value. The food bank was thrilled because they received the full value instead of what would have been left after I paid capital gains tax on a sale. Definitely one of the most tax-efficient moves I've made!

Just to add another perspective - have you considered carpooling with coworkers? My hospital has a similar parking situation but they offer discounted rates for cars with 2+ employees. Four of us share a ride now and split the parking cost, bringing my monthly expense down from $130 to about $35. Plus we take turns driving which saves on gas too.

As someone who works in healthcare administration, I'd strongly recommend exploring ALL your options here. First, definitely talk to HR about pre-tax parking benefits - this could save you $400+ annually. But also look into other hospital programs you might not know about. Many medical centers have financial hardship programs for employees earning under a certain threshold. At $19/hour, you might qualify for parking assistance or subsidies. Also check if your hospital participates in any transit programs - some offer discounted public transit passes or bike storage facilities. Don't forget that as a healthcare worker, you might also qualify for other tax benefits like the Earned Income Tax Credit or education credits if you're taking any continuing education courses. It's worth having a comprehensive review of your entire tax situation, not just the parking issue.

This sounds like a classic case of the IRS processing different parts of your amendment through separate workflows, which is actually pretty common these days! The key thing to focus on is that you got code 846 (Refund Issued) - that's basically the IRS saying "this money is legitimately yours." What's happening is they approved your EIC correction (hence the 768 code and refund) while simultaneously rejecting something else entirely (the 290 code with different reference number). Think of it like they're handling your case in chunks - they fast-track the straightforward stuff like EIC calculations while taking more time to review other items that might need closer scrutiny. The different reference numbers (43277-462-87615-2 vs 89254-638-99014-2) are just their way of tracking different aspects of your case separately. You'll probably get a notice in a few weeks explaining exactly what was disallowed, but it shouldn't affect the refund you already received. My advice: screenshot your transcript, keep your bank deposit records, and feel confident spending that refund. Once the IRS issues an 846 code for something like EIC, they don't typically claw it back. The system actually worked in your favor here, even though the codes look confusing!

I had a very similar experience last year and it really stressed me out until I understood what was happening! What you're seeing is actually the IRS processing your amended return in separate chunks - they approved your EIC correction quickly (hence the 768 code and 846 refund) while still reviewing other aspects of your amendment. The 290 "Disallowed claim" with the different reference number (89254-638-99014-2) is rejecting something completely separate from your EIC issue. The fact that you got the 846 refund code means that money is legitimately yours - once they process a refund for something like EIC, they typically don't reverse it. I was in your exact shoes worrying they'd take the money back, but my tax advisor explained that this chunked processing approach is how they handle complex cases now. You'll probably get a letter in a few weeks explaining what specific item was disallowed, but it won't affect your EIC refund. Definitely take screenshots of your transcript and keep your bank records, but you should be safe to spend that refund. The system actually worked correctly even though those codes make it look contradictory!