I recently went through this exact process and found out something important that hasn't been mentioned yet. If you use any accounting software for payroll (like QuickBooks, Gusto, etc.), they usually require your EIN and legal business name to match EXACTLY what the IRS has on file. So even if you decide to wait for the IRS to process your name change, you might run into issues with your payroll software rejecting submissions in the meantime. When I called my payroll provider, they suggested adding the LLC as a "DBA" of the sole proprietorship in their system as a temporary workaround.

One thing I learned the hard way when I went through a similar transition is to keep detailed records of EVERYTHING during this process. I recommend creating a folder with copies of all correspondence with the IRS, your original EIN confirmation letter, your LLC formation documents, and any letters you send regarding the name change. The reason this is so important is that if there are any discrepancies or issues down the road, you'll need to be able to prove the timeline of your business structure change and that you followed proper procedures. I had an issue 18 months later where the IRS questioned some of my filings, and having that paper trail saved me from potential penalties. Also, make sure you're consistent with how you sign all tax documents during this transition period. Use your legal name as the member-manager of the LLC, not your old sole proprietor signature, even though you're using the same EIN. This helps establish the proper chain of authority for your business entity.

Just wanna point out that TurboTax DOES actually have a way to handle this situation properly, but it's not obvious. Instead of just entering what's in box 10, you need to go to the property tax section and choose "I want to enter my property taxes manually" option. Then it gives you a field to enter your prorated amount with an explanation box where you can note why your number differs from the lender's form.

This is such a common issue that trips up so many new homeowners! I went through the exact same confusion when I bought my first house mid-year. One thing that helped me was creating a simple spreadsheet to track all the numbers - the full year's tax bill, the exact closing date, days of ownership, seller credits, and what my lender reported. Having it all laid out visually made it much clearer that I needed to use the prorated amount based on actual ownership days. Also, don't forget to save your closing statement (HUD-1 or CD) forever - the IRS might want to see how the taxes were allocated at closing if they ever question your deduction amount. I keep mine in the same file as my tax returns for easy reference. The key thing to remember is that tax law is based on actual ownership, not what comes out of your pocket or what your lender reports. You owned the house for X days, so you can deduct X/365 of the annual property tax bill - period. Everything else is just accounting between you and the seller/lender.

Make sure u keep REALLY good records of how u calculated everything!!! I got audited last year for my amazon biz and they questioned my currency conversion methods. Had to provide proof of every conversion rate I used. Without good records I woulda been screwed.

This is really helpful information everyone! I'm dealing with a similar situation but also have sales through Amazon's European marketplaces (UK, Germany, France). Should I be converting all of these different currencies to USD using the same methodology? And does anyone know if there are any special considerations for VAT that gets collected by Amazon on European sales - do I need to account for that differently on my Schedule C since it's not really "my" income?

Has anyone used TurboTax to handle these TD Ameritrade wash sale situations? I'm wondering if importing my 1099-B directly will correctly account for everything or if I need to make manual adjustments.

I've been dealing with this exact issue! One thing that really helped me understand what was happening was creating a simple spreadsheet tracking all my MSFT trades with dates and amounts. When I mapped it out chronologically, it became clear where the 30-day overlaps were occurring. What I discovered is that TD Ameritrade's wash sale identification is actually quite accurate, but their 1099-B presentation can be confusing. The key is understanding that when they show a "W" code next to a transaction, they're not saying that specific sale created a wash sale - they're indicating that the loss from that sale is being disallowed because of a replacement purchase. Also, don't forget that if you have any mutual funds or ETFs that hold MSFT as a major position, purchases of those could potentially trigger wash sales too. It's not just direct stock purchases that count as "substantially identical" securities. The good news is that as long as you report exactly what's on your 1099-B, you should be fine tax-wise. The IRS expects you to use the broker's calculations unless you have a specific reason to believe they're wrong.

Something to consider - check if Box 12 on your W2 has any codes like D, E, F, G, H, S, or similar with amounts listed. These are retirement plan contributions which would reduce the amount shown in Box 1 (wages and compensation) without reducing what you were actually paid. Box 1 on the W2 doesn't show your total compensation - it shows your federally taxable wages after all pre-tax deductions. This is a super common misunderstanding about W2s that causes a lot of panic!

Given that you've ruled out pre-tax deductions and multiple employees have the same issue, this definitely sounds like a systematic payroll error that needs to be addressed. Here's my recommended approach: Document everything first - gather all your paystubs, bank statements showing deposits, and any employment agreements. Calculate the exact discrepancy after accounting for all legitimate pre-tax items. Since your boss is difficult to approach, consider sending a brief, professional email that focuses on the factual discrepancy rather than making accusations: "Hi [Boss], I'm preparing my taxes and noticed my W2 shows $X in Box 1, but my records show I received $Y in gross pay this year. Could you help me understand this difference or arrange for a corrected W2 if needed?" The fact that multiple employees have this issue actually works in your favor - it suggests this isn't about individual employee confusion but rather a processing error. If your employer won't cooperate, the IRS Form 4852 route is completely legitimate in this situation. Don't file with the incorrect amount - it will likely trigger correspondence from the IRS later when they match your employer's quarterly reports with your tax return. Better to resolve this upfront than deal with it during an audit.