Just to clarify, you cannot put a negative number on line 4(c) of the W-4. That line only allows for additional withholding, not reduced withholding. To reduce withholding, you'd need to use line 4(b) to indicate deductions that would lower your taxable income, or line 3 for tax credits and dependents. The IRS won't accept a form with negative values in those fields.

He gets paid every two weeks. I hadn't thought about how the pay frequency might affect things! Does getting paid weekly really help that much with the withholding calculations?

Does the holding period start from the day you sign the purchase papers or the day the sale officially closes? My closing took almost 2 months!

The holding period is generally calculated from the day the first sale closes (when you acquired the property) to the day the second sale closes (when you sold it). The date on the closing documents is what matters, not when you signed the purchase agreement. So in your case, the 2-month closing period would count toward your holding time, which is good if you're trying to reach that 1-year mark for long-term capital gains treatment.

You'll need at least Premier for capital gains from land sales. Deluxe won't handle Schedule D properly. I tried last year and had to upgrade mid-filing.

Thanks for saving me the headache! I'll just go straight for the Premier version then.

Thank you so much for mentioning Form 8833! I just checked my 1042-S and they did apply a treaty benefit (there's something in Box 3 and 4). Will that form be available in regular tax software or do I need something special to file it?

Most major tax software packages like TurboTax, H&R Block, and TaxSlayer have Form 8833 available, but you might need to specifically search for it as it's not always included in the standard interview process. Some of the free filing options might not include this form. When you complete Form 8833, you'll need to reference the specific treaty article that applies to your situation. This information should be mentioned on your 1042-S in Box 13j typically. You'll also need to provide a brief explanation of the treaty benefit you're claiming. Don't worry too much about the technical language - just clearly state what type of income is covered (scholarship, fellowship, etc.) and which country's treaty applies to you.

Is that form 8843 required even if you're just getting a small amount on a 1042-S? I got one for a $500 prize from a contest but I'm a US citizen. Do i still need that form?

That's a really smart idea I hadn't considered! I do have student loans and I've been making payments. Would those interest deductions help in this situation? Also, is it too late to make retirement contributions that would count for last year?

Student loan interest can definitely help lower your MAGI, which is exactly what you want in this situation. You can deduct up to $2,500 in student loan interest depending on your income level. As for retirement contributions, you can still make IRA contributions for 2024 until the tax filing deadline in April 2025. If you have self-employment income, you might also be eligible for a SEP IRA which has higher contribution limits. Just make sure you specify that the contribution is for tax year 2024 when you make it. This is one of the few "retroactive" moves you can make that legally affects your previous year's taxes.

Yes! I successfully did this. The key is that you need to contact the marketplace and specifically request an "income adjustment review" for the previous year. The regular customer service reps often don't know about this process. Ask to speak with a supervisor or advanced resolution team. Explain that you made an honest mistake in reporting your income (confusing net vs. gross) and request the review. They may have you submit documentation of your actual income. In my case, they adjusted my 1095-A and issued a corrected one, which significantly reduced what I owed.

I did mail paper returns for all three years because I had to include some supporting documentation. Did you do anything special to make the process go faster for the 2021 return?

I didn't do anything special for the 2021 return - it just happened to get processed faster. Paper returns are unfortunately at the mercy of whichever processing center they get sent to and how backed up that specific location is. One thing I learned later is that you can actually e-file amended returns for tax years 2019 and later using certain tax software, even with supporting documentation (you can scan and attach PDFs). E-filed amendments tend to process much faster than paper ones. For future reference, that might be a better option if you ever need to amend again.

I did this for my amended returns too. The in-person agent was WAY more helpful than phone support. She even spotted a mistake in my 2019 amendment that would have caused issues and let me fix it on the spot.

That's great to hear your experience was similar! The in-person assistance is definitely underrated. The agents at the Taxpayer Assistance Centers seem to have more time to thoroughly review your situation compared to phone agents who are trying to get through as many calls as possible. I've found they can also sometimes expedite processing if you have a legitimate hardship situation or if there's been an unusually long delay. Did they offer to help speed things up in your case?