I went through this exact same nightmare last year with about 800 trades and numerous wash sales. Here's what I learned after making several mistakes: The key thing to understand is that wash sales MUST be reported individually on Form 8949 - there's no way around this. You cannot include them in summary reporting. However, for your regular trades without adjustments, you can absolutely use the summary method. What worked for me was organizing everything in Excel first. I separated my trades into two categories: those with wash sale adjustments and those without. For the clean trades, I created a single line on Form 8949 that said "Various stocks - see attached statement" and attached a spreadsheet with the totals. For the wash sales, I had to list each one individually. Pro tip: Make sure you're tracking the disallowed loss amounts correctly. The wash sale rule doesn't just defer the loss - it adjusts your basis in the replacement shares. This gets complex when you have multiple wash sales in the same security. TurboTax Premier should handle most of this automatically once you resolve the import issues. The software is actually pretty good at identifying wash sales, but you need to review each flagged transaction to make sure the adjustments are correct. Don't just accept everything blindly. One more thing - keep detailed records of everything. With that many trades, the IRS might want to see supporting documentation if they have questions.

I'm dealing with a similar situation but with an added complexity - I have wash sales that span across tax years. I sold some shares at a loss in late December 2022, then bought them back in early January 2023. From what I understand, the wash sale rule still applies even though the repurchase happened in the following tax year. This means I can't deduct the loss on my 2022 return, and the disallowed loss gets added to the basis of the shares I bought in 2023. Has anyone else dealt with cross-year wash sales? Do I need to make any special notations on my 2022 Form 8949 to indicate that the basis adjustment applies to shares purchased in 2023? I want to make sure I'm documenting this correctly so there's a clear trail when I eventually sell those replacement shares and need to use the adjusted basis. Also, does anyone know if the IRS has specific guidance on how to handle these cross-year situations in tax software? TurboTax seems to be handling it, but I want to make sure it's doing it right.

Just wanted to add some clarity since I see conflicting information in the thread. The situation with separate HDHPs for spouses is actually pretty straightforward once you understand the rules. Since you and your wife have completely separate HDHP policies, you're each eligible for your respective coverage limits. Your plan covering you and your daughter qualifies as family coverage, so your personal HSA contribution limit is $8,550. Your wife's individual coverage gives her a limit of $4,300. The total you can contribute between both HSAs is $12,850 - there's no additional spousal limitation that reduces this amount when you have separate policies. The confusion often comes from scenarios where both spouses are covered under the same family plan, which has different rules. One thing to double-check: make sure your employer (if they contribute to your HSA) and your wife's employer contributions are factored into these limits. Also, if either of you is 55+, don't forget about the $1,000 catch-up contribution you can each make to your respective accounts. The IRS Publication 969 has the detailed rules if you want the official source, but your situation is actually one of the more straightforward ones once you know that separate policies = separate limits.

I've been following this thread closely because I'm in a similar situation with my spouse. We both have separate HDHPs through our employers and were really confused about the 2025 limits too! After reading all the responses here, I wanted to clarify something that seems to be causing confusion. There are actually TWO different scenarios people are mixing up: 1. **Separate HDHP policies** (like you and your wife have) - Each spouse can contribute up to their respective coverage limits with NO spousal limitation. Your family coverage = $8,550 limit, her individual coverage = $4,300 limit, total $12,850. 2. **Both spouses under the same family HDHP** - This is where the spousal limitation rule kicks in, capping total contributions at the family limit of $8,550. The key distinction is whether you're on the same policy or separate policies. Since you have completely separate insurance plans, you're in scenario #1 and can maximize both accounts. I actually called my HSA administrator to confirm this for our situation, and they confirmed that separate policies = separate limits with no additional restrictions. Just make sure to account for any employer contributions when calculating how much you can personally contribute to each account!

Don't forget about the Real Estate Professional status if you spend significant time managing your properties! If you qualify (750+ hours annually in real estate activities and more than half your working time), your real estate losses are no longer subject to the passive loss limitations. This means you could potentially deduct ALL of your losses against other income with no $25k limit or phase-out based on income. This has been a game-changer for my tax situation with my real estate LLC. Just make sure you keep EXTREMELY detailed time logs if you claim this status - the IRS scrutinizes these claims heavily.

Great question! I went through something very similar last year with my rental property LLC. One important thing to add to the excellent advice already given - make sure you're categorizing your $27,500 in repairs correctly between repairs vs. improvements. Regular repairs (like fixing plumbing issues) are fully deductible in the year incurred, but major improvements (like a new roof or HVAC system) typically need to be depreciated over time. The new roof and HVAC might be considered improvements that get depreciated over 27.5 years for residential rental property. However, there are some exceptions - if these were necessary to bring the property up to rentable condition when you first acquired it, they might be treated differently. Also, look into the "safe harbor" rules for small taxpayers - if your average annual gross receipts are $27 million or less (which applies to most individual investors), you might be able to deduct up to $10,000 per building in improvements. Since you're planning to use TurboTax, it should help guide you through these distinctions, but it's worth understanding the difference before you start. Consider keeping detailed records of what exactly was done and why - this documentation could be crucial if you're ever audited.

I've been dealing with IRS phone issues for months and finally found a method that works consistently! Try calling the Taxpayer Assistance Center line at 1-844-545-5640 instead of the main number. This line is specifically for people who need help navigating IRS services and they're usually much better staffed. When you get through (typically 15-30 minute wait), explain that you've tried the main line multiple times without success and they can either help you directly or transfer you to the right department with priority status. Also, if you have a smartphone, download the IRS2Go app and check if you can resolve your issue through their online services first - sometimes you can get transcripts, payment history, or status updates without needing to call at all. The app has gotten much better over the past year. One more tip: if you're dealing with a notice or letter, take a photo of it and have it ready on your phone. The agents can often resolve issues much faster when they can see exactly what correspondence you received. Good luck - the system is frustrating but you'll get through eventually!

I've been lurking here reading everyone's advice because I'm in the exact same boat - needed to reach the IRS about a transcript issue and was getting nowhere with the main line. Just wanted to share that I tried @Grace Patel's suggestion about the Taxpayer Assistance Center line (1-844-545-5640) this morning and got through in about 18 minutes! The agent was incredibly helpful and actually transferred me to the right department without me having to start over. For anyone wondering about the menu system - it's much simpler than the main line. Just press 1 for English and then you're in a queue for an actual person. No complicated button sequences needed. The agent I spoke with said this line is specifically designed for people who are having trouble with the regular system, which explains why it's so much more efficient. Thanks to everyone who shared their experiences here - this community is a lifesaver when you're dealing with IRS frustrations! 🙏

I'm in almost the exact same boat as you! Made about $8,200 last year doing freelance writing and web content, and yeah - that self-employment tax hit was brutal. What really helped me understand it better was realizing that as a 1099 contractor, you're essentially running a small business in the eyes of the IRS, even if it doesn't feel that way. One thing that saved me some money was being more aggressive about tracking business expenses. I started using a simple spreadsheet to log everything - even small stuff like printer paper, ink cartridges, and that ergonomic mouse I bought specifically for work. Those $15-30 purchases throughout the year added up to almost $400 in deductions I would have missed otherwise. Also, if you have a dedicated workspace at home (even just a corner of a room), make sure you're claiming the home office deduction. For my 120 sq ft workspace in my 1,200 sq ft apartment, I could deduct 10% of my rent, utilities, and renter's insurance. That was another $800+ in deductions. The 15% you're setting aside sounds about right for self-employment tax, but don't forget you might get some of that back if you qualify for things like the Earned Income Tax Credit. Definitely worth double-checking all the credits available for lower-income taxpayers!

I totally feel your pain on this! I'm a freelance photographer making similar amounts and had the exact same shock last year. What helped me was understanding that the 15.3% self-employment tax is basically covering your Social Security and Medicare contributions that an employer would normally split with you. One thing that really saved me money was getting serious about mileage tracking. I use a simple app on my phone to log every trip to client meetings, the camera store, or even driving to scout locations. At 65.5 cents per mile, this added up to over $600 in deductions last year that I would have completely missed. Also, since you're in graphic design, make sure you're deducting your internet bill (business portion), any co-working space fees if you use those, and professional development like online courses or design conferences. Even webinars and virtual workshops count as business expenses. The tax system definitely feels unfair to small freelancers, but once you get good at tracking everything and understand the rules, you can minimize that bite. I now set aside 20% just to be safe and usually get a little refund, which feels way better than owing money in April!