I completely understand the confusion around W-9 forms - I went through the exact same thing when I started my consulting business! The privacy concerns are totally valid, but unfortunately the IRS doesn't give much wiggle room on this. Here's the bottom line: Line 1 of the W-9 must match exactly how you file your taxes. As a sole proprietor, that means your legal personal name goes on line 1, period. Your business name or DBA would go on line 2. Even if you form a single-member LLC later (which is the default structure), you'll likely still use your personal name on line 1 because most single-member LLCs are "disregarded entities" for tax purposes - meaning the income flows through to your personal tax return. The only time you'd put a business name on line 1 is if your LLC elects to be taxed as an S-Corp or C-Corp, because then the business files its own separate tax return. I know it's frustrating from a privacy standpoint, but any mismatch between your W-9 and tax filing will trigger automated IRS notices. I learned this lesson the hard way! For privacy protection, I'd suggest looking into getting a virtual business address or registered agent service rather than trying to work around the name requirements. That way you can keep your home address private while still following all the IRS rules exactly. It's not a perfect solution, but it's the best balance between privacy and compliance that I've found.

This thread has been incredibly helpful! I was in the exact same position as the OP - trying to balance privacy concerns with IRS compliance requirements. After reading through everyone's experiences, I'm convinced that following the name matching rules exactly is the only safe approach. I ended up going with the single-member LLC route (keeping my personal name on line 1 of W-9s since it's a disregarded entity) and got a virtual business address through one of the services mentioned here. It's not perfect privacy, but it's the best compromise I could find that keeps me fully compliant while protecting my home address. One thing I'd add for anyone still on the fence - I called the IRS directly using that Claimyr service someone mentioned earlier in the thread, and the agent confirmed everything that's been discussed here. Having that official confirmation really gave me peace of mind about my approach. Thanks to everyone who shared their real-world experiences - it saved me from making costly mistakes!

22 Quick question - does anyone know if the threshold for 1099-K reporting is staying at $600 for 2025 filing, or is it going back up? I sell stuff on eBay occasionally and I'm trying to figure out if I need to worry about this for next year.

I've been dealing with a similar situation and wanted to share what I learned from my tax preparer. The reason most tax software pushes you toward Form 8949 instead of Schedule 1 line 24z is that line 24z is typically reserved for specific types of income adjustments that don't involve capital transactions. For personal items sold at a loss (like your furniture and electronics), the IRS considers these capital transactions, even though they're personal property. This means Form 8949 is technically the correct form, despite feeling overly complicated for what should be simple. One thing that helped me was realizing I could summarize similar items rather than listing every single transaction. For example, "Various household items sold on PayPal - 15 transactions" with total proceeds and estimated cost basis. As long as you can reasonably justify your basis estimates and keep any receipts or records you do have, this approach is acceptable and much more manageable than itemizing everything separately. The good news is that once you set it up correctly in the tax software, it automatically handles all the calculations and transfers the information to the right places on your return.

Has anyone tried the IRS Free File Fillable Forms for this? I know it's not as user-friendly as the guided software, but it should theoretically support all tax forms and codes including Schedule D with Code L on Form 8949, right?

I ran into this same issue last tax season! After trying several free options that didn't support Code L, I ended up using the IRS Free File Fillable Forms that Zoe mentioned. Yes, it's more manual work, but it's completely free and supports all codes. For anyone going this route: you'll need to calculate your own gains/losses and manually enter each transaction on Form 8949. Code L is for when basis wasn't reported to the IRS (which is typically the case with 1099-K from personal property sales). The key is documenting your original cost basis - even rough estimates are acceptable for personal items you sold at a loss. One tip: keep detailed records of how you determined your cost basis in case of questions later. I made a simple spreadsheet showing item descriptions, estimated original purchase dates/prices, and sale amounts. Made the whole process much smoother.

Has anyone else had Tax Act just completely crash when trying to enter Marketplace information? I've been trying for hours and the program freezes every time I get to the 1095-A section. Starting to think I should switch to a different software...

I had this exact same frustration last year! The 25-character limit in Tax Act (and honestly most tax software) is super annoying when you're staring at that ridiculously long policy number on your 1095-A. What worked for me was entering just the first 25 characters exactly as they appear, making sure not to include any spaces or dashes that might be formatting. The IRS matching system is designed to work with partial policy numbers - they know the software has these limitations. One tip: double-check that you're copying from the right box on your 1095-A. Sometimes there are multiple numbers on the form and you want the actual policy identifier, not a transaction number or something else. Box A should have your policy number. Don't stress too much about this - it's way more common than you'd think and the IRS systems handle truncated policy numbers just fine. Your refund won't be delayed over this!

This has been such an informative discussion! I'm dealing with a very similar situation with some pharmaceutical stocks my father gifted me about 6 months ago. He had held them for over 3 years, so based on what everyone's shared here, I should qualify for long-term capital gains treatment when I sell. One additional tip I wanted to share - if you're working with an older family member who gifted you stocks, it might be worth checking if they have old paper stock certificates stored away. My dad had completely forgotten about some physical certificates he kept in a safety deposit box from the 1980s and 90s. Those certificates had the original purchase dates and sometimes even the price paid written right on them or on attached documentation. It's becoming less common with electronic trading, but for stocks purchased decades ago, physical certificates might still exist and could be a goldmine of information for establishing cost basis and holding periods. Worth asking your gift giver to check any old files or safety deposit boxes they might have! @Lauren Zeb - Thank you for the professional insights, especially about the dual-basis rules. That's exactly the kind of complex scenario that would have tripped me up without proper guidance.

This thread has been incredibly helpful! I'm actually a CPA who specializes in gift and inheritance tax issues, and I wanted to add one important point that hasn't been mentioned yet. For those dealing with gifted stocks, you should also be aware of the potential impact of state taxes. While federal capital gains rules are fairly standardized, state treatment can vary significantly. Some states don't tax capital gains at all, while others treat them as regular income. If you've moved states since receiving the gift, or if the original owner lived in a different state, there might be additional complexities to consider. Also, I've seen several people mention various online tools and services. While these can be helpful, I'd strongly recommend having any significant gift stock transactions reviewed by a tax professional, especially if the amounts are large or the situation involves any of those dual-basis scenarios Lauren mentioned. The cost of professional review is usually much less than the potential penalties and interest from getting it wrong. One last tip - if you're planning to sell gifted stocks, consider the timing carefully. If you're close to a year-end and have other capital gains or losses for the year, strategic timing of the sale might help optimize your overall tax situation through gains/loss harvesting strategies.