Thanks for this info! I had no idea the IRS could help with missing W2s or that employers had a deadline for sending them. My company is definitely past that February 15th deadline now so maybe that's why they're being so slow about it. I'll definitely try calling that number. Do you know if there's a way to check online whether my employer has already submitted my W2 info to the IRS? That would save me time on the phone if I could see it's already in their system.

Unfortunately there isn't an online way to check if your specific W2 has been filed with the IRS yet. The only way to get that information is by calling them directly. One thing you might try though is creating an account on the IRS website (if you don't already have one) at irs.gov/account. While it won't show your current year W2 info before you file, it will at least give you access to request a wage and income transcript from previous years, which can be helpful for reference.

This is the most important advice in the thread honestly. The extension is ONLY for filing paperwork, not for paying what you owe! I think a lot of people don't realize this.

Thanks for this suggestion! I just tried accessing my transcript online but it looks like it only shows forms that have already been processed by the IRS. Since my client is late sending the 1099, it's not showing up there yet. But this is definitely good to know for the future or if I need to verify what's been reported under my SSN.

What if the amount I calculate from my records is different from what eventually shows on the 1099 when they finally send it? Will that cause problems with the IRS?

Wait, I thought the special rule for charitable donations when taking the standard deduction expired after 2021? Is that still available for 2023?

You're absolutely right, and I apologize for my error. The special provision that allowed taxpayers to deduct charitable contributions while taking the standard deduction was temporary and has expired. For 2023, you would need to itemize deductions on Schedule A to claim charitable contributions. Thanks for the correction - it's important to have accurate information when making these last-minute tax decisions!

Good point! Most online platforms have a dropdown or option to select which tax year the contribution is for, but it's easy to miss. I always take a screenshot of the confirmation page showing the tax year just to be safe.

That's a smart approach with the screenshot! I've started doing something similar. When I make my contribution now, I actually call my financial institution afterward to verbally confirm they've recorded it for the correct tax year, then note the date, time and representative's name. It takes an extra few minutes but saves potential headaches later.

Do you need to collect sales tax based on where your business is located or where your customers are? I ship to people all over the country and I'm so confused about this part.

You need to collect based on where your customers are located, not where your business is. This is called "destination-based" taxation and most states use this approach. So if you're in Texas but shipping to a customer in California, you'd charge California sales tax (assuming you have nexus in California). Each state has different rules for when you establish "nexus" (the obligation to collect), but generally it's based on either physical presence (having inventory, employees, etc. in the state) or economic presence (selling over a certain dollar amount or number of transactions to customers in that state).

I tried doing spreadsheets but it got so complicated with different tax rates in different counties and cities. What do you do when you have to calculate different rates for different customers?

Does the election apply to all securities you trade or can you designate only certain accounts? I do both long-term investing and active trading but keep them in separate accounts.

The election applies to all your securities that are part of your trading business. The key is proper segregation. If you have legitimate investment accounts that are clearly separated from your trading accounts, you can keep those as capital assets subject to regular capital gains treatment. You'll need to clearly document this separation ahead of time and be consistent in how you treat those accounts. Many traders maintain separate accounts - one for long-term investments (capital asset treatment) and others for active trading (mark-to-market treatment).

Is there a specific form for the estimated payments or just the regular 1040-ES? And how do you calculate if your trading income varies wildly month to month?

You use the regular 1040-ES for the payments. For wildly varying income, you have two options: you can either pay based on your actual income for each quarter (which requires more calculation but can match your cash flow better), or use the "safe harbor" provision by paying 100% of last year's tax liability (110% if your income was over $150,000). I personally track my trading P&L monthly and adjust my quarterly payments accordingly. It's more work but prevents overpayment when I have down quarters. Just make sure you're keeping detailed records of your calculation method in case of questions later.