Thank you so much for sharing the exact location! I've been stuck on this same error for two days and was getting ready to give up on H&R Block entirely. Just checked under "State and Local" > "Locality Information" and there it was - the county dropdown that I never would have found otherwise. You're absolutely right about their error message being misleading. When it says "add your County Name" you'd naturally think to look in your personal/address information, not buried in a state tax section. It's like they designed the interface to be as confusing as possible. For what it's worth, I'm in Pennsylvania and the field was in the exact same place you described. Hopefully this helps other people avoid the same frustration!

This is such a helpful way to think about it! I've been stressing about this for weeks and your two-transaction breakdown makes it so much clearer. I was getting overwhelmed trying to understand why the same money seemed to appear on both forms, but separating the exercise from the sale mentally really helps. So just to confirm my understanding - the $72K on my W-2 is from the "exercise" part (getting $92K worth of stock for $20K), and then the 1099-B is just documenting that I immediately converted that $92K in stock back to $92K in cash. No wonder there's basically no gain or loss on the actual sale part! Thank you for breaking it down this way - it's going to make entering everything into my tax software much less stressful.

This is exactly the kind of clear explanation I needed! I've been going in circles trying to understand this for days. Your breakdown of the "bargain element" concept really helps - I didn't realize that's what they call the difference between the exercise price and market value. One quick follow-up question: when you mentioned using Form 8949 for the basis adjustment, did you have to attach any additional documentation to explain the adjustment, or does the form itself provide enough detail for the IRS? I want to make sure I don't trigger any red flags or get a notice later asking for more information. Also, did your tax software automatically prompt you about the stock option situation, or did you have to specifically look for where to make the adjustment? I'm using FreeTaxUSA this year and want to make sure I don't miss anything important.

That's really helpful to know that support confirmed it's a system-wide issue! I was getting worried that something was wrong with my specific account. It's frustrating that they can't give a timeline, but at least we know they're aware of the problem. I'm curious about your experience with taxr.ai - how long did it take you to get your documents processed and was the interface pretty straightforward? I'm considering making the switch too since I'd rather not deal with potential future outages, especially this close to the deadline. Thanks for sharing both solutions!

@b382224f7ba6 Thanks for confirming with support! That's really reassuring to know it's not account-specific. I'm definitely going to check out taxr.ai based on all the positive feedback here. How accurate was the document scanning for you? I've got some pretty complex forms this year including some 1099-MISC income and I'm always worried about automated systems missing important details or decimal points.

I can share my experience with taxr.ai on rental property forms! I had Schedule E forms from two different rental properties last year, and the scanning handled them really well. It picked up all the rental income, expenses, and even the depreciation amounts correctly. The system seems to be specifically designed to handle the more complex tax forms that give other software trouble. For small business forms, I only had a simple Schedule C, but it processed everything accurately including business expenses and mileage deductions. The interface actually walks you through reviewing all the extracted data before finalizing, so you can catch any potential issues before submitting. Given how unreliable FreeTaxUSA's servers have been lately, having a backup that can handle complex forms is definitely worth considering!

@7007be7e7758 I've been using taxr.ai for my consulting business forms and it's handled Schedule C really well, including all the complicated business expense categories. The scanning even picked up my home office deduction details from the supporting documents I uploaded. One thing I really like is that it shows you exactly what it extracted from each document so you can verify everything before moving forward. For rental properties, it correctly identified all my Schedule E income and expense items, even when some of the property management statements had weird formatting. The accuracy has been way better than I expected, especially for the more complex business forms that usually require a lot of manual double-checking.

This is a really comprehensive overview that ties together all the key points from this discussion. Your point about timing is especially important - I was initially thinking about trying to make the 2024 election work, but you're absolutely right that focusing on 2025 gives me much better preparation time. The math on my capital losses is pretty compelling when you lay it out like that. Spreading $9,750 in losses over multiple years at the $3,000 annual limit versus deducting it all immediately through MTM is a significant difference in tax impact. I'm going to start that trading journal immediately and begin documenting my time and business activities. Even though I've been trading at this volume for months, I haven't been treating it with the business-like documentation that would support a trader status election. One thing I'm still wrestling with is whether to use separate brokers for my trading versus long-term positions, as mentioned in earlier comments. Right now everything is in my Fidelity account, but it sounds like clear separation might be important for maintaining different tax treatments. Have you seen traders successfully maintain this separation within a single brokerage, or is using different brokers really the safer approach?

Regarding account separation within a single brokerage - this is actually a gray area where different tax professionals have varying opinions. Some CPAs I've consulted with say you can maintain separation within one brokerage by clearly designating accounts for different purposes (like having a "Trading" account and "Long-term Investment" account both at Fidelity), while others strongly recommend using completely different brokers to eliminate any ambiguity. The safer approach is definitely separate brokers, but it's not always practical. If you do stay with one brokerage, make sure you: 1. Open distinctly named accounts (not just "Account 1" and "Account 2") 2. Never transfer securities between the accounts 3. Maintain completely different trading strategies and holding periods 4. Document in writing the purpose of each account 5. Keep detailed records showing the business vs. investment intent The IRS will look at your actual behavior more than the account structure. If you're consistently day trading in one account and buy-and-hold investing in another, that pattern matters more than which brokerage houses them. That said, using different brokers does provide cleaner documentation and eliminates potential questions during an audit. If the hassle of managing multiple brokerages isn't too burdensome, it might be worth the extra protection. Whatever you decide, document your reasoning and stick to it consistently. The worst thing you can do is mix strategies between accounts or change your approach mid-year.

Thank you for sharing your real-world experience with the MTM election - this is exactly the kind of practical insight that helps paint the full picture. Your point about the ongoing administrative burden is something I hadn't fully considered. 2-3 hours monthly for record-keeping seems manageable, but it's good to know upfront what I'm signing up for. The reality check on ordinary income vs. capital gains treatment is also crucial. Right now I'm focused on the immediate benefit of deducting my accumulated losses, but you're absolutely right that I need to think long-term about how this affects future profitable years. Given that most of my trades are very short-term anyway (2-3 minutes), I'm probably not benefiting much from capital gains rates currently, but it's still an important consideration. I really like your approach to the employment documentation - creating a proactive memo about trading policies seems like a smart way to demonstrate awareness of potential conflicts without making it a big deal. I'm going to draft something similar. One follow-up question about your experience: How has the relationship with your CPA evolved over the three years since making the election? Are you still paying for specialized help each year, or have you been able to take on more of the routine compliance work yourself as you've gotten familiar with the requirements? The learning curve concern is noted - I'd rather understand the full commitment upfront than be surprised by complexity later.

Great question about the CPA relationship evolution! After three years with MTM, I've been able to take on much more of the routine work myself. The first year, I paid about $1,200 for full-service preparation since everything was new and I needed guidance on proper documentation and reporting formats. By year two, I was handling most of the data organization and basic calculations myself, and my CPA fees dropped to around $400-500 for review and filing. Now in year three, I do almost all the prep work and just pay for a final review ($200-300), unless there are unusual situations that need professional interpretation. The key was investing time upfront to really understand the MTM reporting requirements and building good systems. I created templates for tracking year-end positions, standardized my trading journal format, and learned to properly categorize business expenses. Once you understand the framework, a lot of it becomes routine data entry. That said, I still value having professional oversight. Tax law changes, and there are always edge cases that benefit from expert review. But the ongoing costs have become much more manageable as I've gained experience with the requirements. The first year is definitely the steepest learning curve, both for understanding the tax implications and building good record-keeping habits. But if you're already disciplined about tracking your trades (which you'd need to be anyway), the additional administrative work for MTM becomes pretty manageable once you get the systems in place.

This! So many people get confused about S-Corp rules. The "reasonable compensation" requirement doesn't disappear just because you're not profitable. My tax guy says the IRS specifically looks for this during audits of S-Corps.

This is really helpful context! I'm new to S-Corp taxation and was wondering - when you mention the loss flows through proportionally on K-1s, does that mean if my brother owns 50% but takes no salary/distributions, he still gets 50% of the loss allocated to him? And would that loss potentially help offset his other income even though he didn't contribute to generating it this year?