Just wanted to share that this exact thing happened to a friend of mine at our company. Turns out there was a glitch in the payroll system that affected some employees but not others when they implemented the new withholding tables. The people who had submitted a new W-4 form after 2020 were fine, but people using their old W-4 settings got weird withholding amounts. When my friend finally figured it out and confronted HR, they admitted that they knew about the issue but didn't notify affected employees because they "assumed people would notice on their paychecks." Pretty frustrating! Definitely check with your HR department.

If you want to avoid this kind of issue in the future, use the IRS Tax Withholding Estimator tool on their website. I check mine every January and June to make sure I'm on track. You can adjust your withholding mid-year if something looks off.

Has anyone actually had the IRS question or audit them specifically about capital losses? I'm carrying forward about $22k in losses from some terrible crypto investments and wondering how careful I need to be with documentation.

Just wanted to add some perspective as someone who's been through this exact situation. I had about $15k in capital losses from some poor investment choices early in my career when I was making very little money. Like you, I wished I could save them for when my income was higher. The reality is that even though you have to take the $3,000 deduction each year, it's still beneficial in low income years. That $3,000 deduction might only save you a few hundred dollars now, but it's guaranteed tax savings versus hoping your future income will be higher. Plus, there's always the risk that tax laws could change in the future. One thing that helped me was tracking exactly how much I was saving each year from the capital loss deduction. Even in my lowest earning years, that $3,000 deduction was putting real money back in my pocket that I could invest or save. Over the 5 years it took to use up my losses, the total benefit was substantial. Keep good records of your carryforward amounts each year - it makes tax filing much easier and you'll want that documentation if the IRS ever has questions.

Just an FYI - make sure you're keeping detailed records of how much you use the trailer for business vs personal use. The IRS has been cracking down on this lately. I keep a logbook in my trailer and note every use, the purpose, and mileage. Has saved me a couple times when questions came up. Also, take plenty of photos of the trailer being used for business purposes throughout the year. Documentation is your best friend if you ever get audited!

Great question about the trailer depreciation! I'm also a small business owner and dealt with similar equipment purchases. One thing I'd add to the excellent advice already given - make sure to consider the timing of when you place the trailer "in service" for your business. The IRS requires that you actually start using the asset for business purposes before you can claim any depreciation. So if you bought it in December 2024 but didn't start using it for landscaping jobs until January 2025, you'd need to wait until your 2025 tax return to start claiming the depreciation. Also, since you mentioned this is your first major equipment purchase, you might want to look into whether you qualify for the small business exemption from certain record-keeping requirements. If your business gross receipts are under $27 million (which sounds likely for a landscaping operation), you have some flexibility in how you account for these purchases. The 60% bonus depreciation for 2024 that Aisha mentioned is spot-on, but don't forget you can also elect out of bonus depreciation if regular MACRS gives you better tax planning benefits spread over multiple years.

can someone explain why we even need to worry about this ein stuff when converting? i mean i get that an llc gives you liability protection but why does the irs care if its the same business just with a different legal structure?? seems like unnecessary bureaucracy to me.

Just went through this exact conversion process a few months ago and can confirm what others have said - you definitely need a new EIN for your LLC. The confusion often comes from people thinking they can "transfer" an EIN, but that's not how it works. Here's what I learned: Your DBA is tied to your personal SSN or sole proprietor EIN, while your LLC is a completely separate legal entity that needs its own tax identification number. Think of it like this - if you were to close your LLC tomorrow, your personal tax obligations would still exist separately. The process is actually pretty straightforward once you understand it: 1. File your LLC formation docs with your state first 2. Apply for a new EIN online at irs.gov (takes 5 minutes, get it instantly) 3. Use your old EIN for final sole proprietor tax filings 4. Start using your new EIN for all LLC business going forward Don't overthink it - the IRS chat service is notoriously unhelpful for specific questions like this. The online EIN application is really the easiest route. Just make sure your LLC paperwork is filed with your state before applying for the EIN.

For anyone still having trouble, I found out TurboTax is doing system maintenance every night from 1am-3am EST right now. That's why uploads might work at some times but not others. Their support chat told me to try during business hours for best results. Apparently they're dealing with higher than normal volume this season.

Just wanted to add my experience after reading through all these responses - I had the same upload errors for days and tried everything mentioned here. What finally worked for me was completely logging out of TurboTax, clearing all my browser data (not just cache, but cookies and stored data too), then logging back in. Apparently there was some corrupted session data that was causing the uploads to fail. After doing a fresh login, all my documents uploaded immediately without any errors. Might be worth trying this simple step before going the third-party route or waiting hours for support!