I've been dealing with this exact same confusion! As someone who recently went through the sole proprietor to LLC transition, I can definitely confirm what everyone else is saying about the IRS being super strict on name matching. The key thing I learned is that it's not about what you WANT to put on the W-9, it's about what you're REQUIRED to put based on how you file taxes. If you're a sole proprietor now, your personal legal name absolutely has to go on line 1, even if you have a business name. The business name goes on line 2. When I formed my single-member LLC, I was disappointed to learn I still had to use my personal name on line 1 since it's a "disregarded entity" for tax purposes. My income still flows through to my personal tax return, so that's the name that has to match. For privacy, I ended up getting a virtual business address instead of trying to work around the name requirements. It's not perfect, but at least my home address isn't on business documents anymore. The virtual mailbox service runs about $20/month and has been worth it for the peace of mind. Don't try to get creative with the IRS rules - I've seen too many people in this thread share horror stories about mismatch notices and the months it takes to resolve them. Better to follow the requirements exactly and find other ways to protect your privacy!

As someone who went through this exact same confusion when starting my freelance business, I totally get the privacy concerns! Unfortunately, the IRS is extremely rigid about name matching between your W-9 and tax returns - their automated systems will flag any discrepancies and trigger those dreaded CP2000 notices. Here's what I learned after consulting with a tax professional: If you're currently a sole proprietor, your legal personal name MUST go on line 1 of the W-9, period. Any business name or DBA goes on line 2. This is because you file taxes under your personal name and SSN as a sole proprietor. Even if you form an LLC later, if it's a single-member LLC with default tax treatment (which is most common), you'll still need to use your personal name on line 1 because it's considered a "disregarded entity" for tax purposes - meaning income flows through to your personal return. Only if you elect S-Corp or C-Corp treatment would you put the business name on line 1. For privacy protection, I'd recommend looking into a virtual business address or registered agent service instead of trying to work around the name requirements. That way you can keep your home address private while staying fully compliant with IRS rules. It's not perfect privacy, but it's the best legal compromise I've found. Trust me, it's better to follow the rules exactly than deal with months of IRS correspondence later!

I'm currently dealing with this exact same situation and this thread has been absolutely invaluable! I formed my LLC in Delaware back in 2022 for a freelance consulting business that never really got off the ground. I filed dissolution paperwork with the Delaware Division of Corporations about 6 months ago, thinking that was all I needed to do. Just last week I received a letter from the IRS asking about my 2024 filing requirements, which totally caught me off guard since I thought everything was closed. Reading through everyone's experiences here, it's crystal clear that I made the same mistake as most people - assuming state dissolution automatically handles the federal side too. The consensus from this thread is really helpful: call the IRS Business line at 800-829-4933 to check EIN status, file a final tax return with the "final return" box checked (even with $0 income), and send written notification to the IRS about permanently ceasing operations. What I find most reassuring from all these responses is that the IRS agents are apparently understanding about this being a common oversight. I was really worried about penalties or complications, but it sounds like this is fixable as long as you take action promptly. I'm planning to make that IRS call tomorrow morning and get this sorted out once and for all. Thanks to everyone who shared their experiences - you've probably saved me years of confusing penalty notices!

This entire thread has been such an eye-opener! I'm a small business owner who went through LLC dissolution last year and made exactly the same mistake everyone is describing here. I filed my state paperwork thinking I was completely done, only to get IRS letters months later. What I learned from my experience (and what this thread confirms) is that the IRS Business line at 800-829-4933 really is your best first step. The agents there are incredibly knowledgeable about LLC closures and can immediately tell you your exact status in their system. They walked me through everything I needed to do, including filing that crucial final return with the "final return" box checked. One additional tip I didn't see mentioned much here: if you're unsure about any of your LLC's tax elections or filing history, ask the IRS agent to review your business account while you're on the call. They can see everything - whether you made any special elections, what returns were filed, etc. This saved me from guessing about which forms I actually needed. The peace of mind you get from properly closing everything with the IRS is absolutely worth the small effort. Don't let this drag on - that letter you received is actually a good thing because it means they have you in their system and can easily process your closure once you file correctly. You've got this!

I'm so sorry this happened to you! As someone who works in tax preparation, I can tell you that $470 for 17 crypto transactions is absolutely outrageous. That works out to over $27 per transaction, which is highway robbery. Here's the reality: most crypto transactions from major exchanges like Coinbase are actually pretty straightforward to report. Coinbase provides detailed tax documents (Form 1099-B) that include all the information you need - purchase dates, sale dates, cost basis, and proceeds. There's no "manual blockchain verification" needed when you have proper exchange documentation. For future reference, here are much more reasonable options: - Most major tax software (TurboTax, TaxAct, FreeTaxUSA) now handle crypto imports directly - A reputable tax professional should charge $5-15 per transaction MAX, or a flat fee of $100-200 for crypto handling - Many crypto tax platforms like Koinly or CoinTracker can organize everything for under $100 I'd seriously consider filing a complaint with H&R Block corporate about this pricing. They took advantage of your unfamiliarity with crypto taxes to massively overcharge you. Don't let them make you feel like crypto taxes are some impossible mystery - they're really not that complicated with the right tools and documentation.

This is absolutely outrageous! I work as a tax preparer and can tell you that $470 for 17 crypto transactions is completely unreasonable. Most professionals charge between $5-15 per transaction or a flat fee of $100-200 for crypto work. The "specialized expertise" and "manual blockchain verification" they claimed is mostly marketing nonsense. If you provided your Coinbase transaction history (which includes all necessary cost basis and date information), there's no need for complex verification against blockchain records. For next year, I'd strongly recommend trying tax software with built-in crypto support like TurboTax, TaxAct, or FreeTaxUSA. These can import your Coinbase data directly and handle the calculations automatically for a fraction of what you paid. You should also consider filing a complaint with H&R Block corporate about this pricing. They clearly took advantage of your unfamiliarity with crypto taxes to massively overcharge you. Don't let them make you think crypto taxes require some impossible level of expertise - with proper exchange documentation, they're actually quite straightforward to handle.

Don't forget that you might need Form 8606 even if you don't need Form 5329! Form 8606 is used to track the basis in your Roth IRA and to determine how much of a distribution is taxable if it's not fully qualified.

Based on what you've described, you should be all set without Form 5329! Since you're over 59.5 and your Roth IRA is more than 5 years old, this is indeed a qualified distribution that won't require any additional forms or penalty calculations. When you enter your 1099-R in TurboTax, just make sure you answer the questions about your age and account age correctly. The software should automatically recognize it as a qualified distribution and handle everything properly. Even if the distribution code in box 7 of your 1099-R isn't perfect, TurboTax will override that based on your responses to their questions. The 1099-R will still appear on your tax return for reporting purposes, but there won't be any tax consequences. Form 5329 is really only needed when there are penalties to calculate or exceptions to claim for early distributions.

Another point to consider - make sure you're keeping track of any expenses you have between inheritance and sale. Property taxes, maintenance costs, repairs, and selling expenses (like realtor commissions) can all be added to your basis or subtracted from the sales price. So your calculation would be: Sales price - (FMV at date of death + improvements/expenses) = gain/loss Even if you use the sales price as evidence of FMV at date of death, you can still deduct those carrying costs from your proceeds. This is especially important if you had to do any repairs or maintenance to get the property ready for sale.

Great thread with lots of helpful information! I wanted to add one important point that hasn't been mentioned yet - make sure you understand the difference between the estate's tax obligations and your personal tax situation. If the estate was large enough to require filing an estate tax return (Form 706), the executor may have already had the property appraised as of the date of death. In that case, you'd want to use that appraised value as your basis rather than the sales price, even if the sales price is higher. Also, since you mentioned getting multiple cash offers that are higher than expected, be prepared to document that these are legitimate arms-length transactions with unrelated buyers. The IRS might question unusually high sales prices, especially if they seem out of line with local market conditions. Keep records of all the offers you received and any market analysis your realtor provided. One last tip - consider consulting with a tax professional who specializes in estate and inheritance issues before you finalize the sale. The relatively small cost of professional advice could save you significant money and headaches down the road, especially given the amounts involved.