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Skylar Neal
Has anyone tried the "two jobs" checkbox in Step 2 of the W4? My husband and I both work and I was thinking that might be easier than trying to calculate everything precisely. Would that work for a situation with commission income too?
I tried the checkbox approach last year and it overwithhheld by quite a bit. We got a $4800 refund which was nice but meant our paychecks were smaller all year. The checkbox basically assumes both jobs make about the same amount, so if there's a big difference in your incomes, it might not be the best option.
Ella Harper
ā¢The "two jobs" checkbox is designed primarily for couples where both jobs have relatively similar pay. It uses a standard calculation that essentially doubles the withholding rate on both paychecks to account for the combined income pushing you into higher tax brackets. With commission income involved, the checkbox method isn't ideal because it doesn't account for the variability. It would likely result in significant overwithholding during months when commissions are low, and potentially underwithholding when commissions are high. For your situation, either the withholding estimator or the more detailed multiple jobs worksheet would give you more accurate results. If you want something simple but more tailored than the checkbox, you could use the IRS Tax Withholding Estimator once to get a baseline additional withholding amount, then add that to line 4(c) of your W4.
One thing I haven't seen mentioned yet is the importance of considering state taxes in your W4 calculations, especially if you live in a high-tax state. The federal W4 estimator is great for federal withholding, but don't forget that commission income can also bump you into higher state tax brackets. In our case (similar situation - dual income with variable bonuses), we found that we needed to increase our state withholding too. Some states have their own withholding calculators, but if yours doesn't, a good rule of thumb is to add your state's top marginal rate as additional withholding on commission income. Also, since you mentioned your commission varies "quite a bit," consider doing a mid-year check-up around July or August. Run the numbers again with your actual year-to-date income and commission, then adjust if needed. This prevents end-of-year surprises and is especially important in years when your commission pattern changes significantly from what you initially estimated.
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Has anyone had to file an amended return because of a corrected 1099? I'm in a similar situation but I already filed my taxes last week, and now I'm seeing that my 1099-DIV from Schwab might have some errors. Will the IRS automatically flag this or should I be proactive and file an amended return?
You should definitely file an amended return using Form 1040-X once you receive the corrected 1099. The IRS will likely catch the discrepancy through their matching program, but it's better to be proactive than to wait for a notice. The good news is that if the correction results in you owing more tax, as long as you file the amendment before the IRS contacts you about it, you'll typically avoid any accuracy-related penalties. You might still owe interest on any additional tax, but that's usually minimal if you amend quickly.
Nora Bennett
I dealt with a similar Robinhood 1099 issue last year. One thing that helped me was downloading my full transaction history from Robinhood's web platform (not just the monthly statements) and doing a line-by-line comparison. Sometimes the discrepancies come from how they categorize certain transactions or handle stock splits. Also, make sure you're looking at the right boxes on the 1099 - qualified dividends vs ordinary dividends are reported separately, and sometimes what looks like an error is just dividends being split between different categories. If you find a genuine error after double-checking everything, Robinhood's tax support team is actually pretty responsive during tax season. I got my corrected form in about 10 business days. Don't stress too much about the audit risk - 1099 corrections are extremely common and the IRS expects them. Just make sure you file with the correct information once you have it.
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CosmicCadet
Looking at this from another angle - there's a bigger issue with how these high-value artifact/art donations work. The whole "buy for X, appraise for 3X, then donate" approach seems problematic regardless of whether the items were stolen. The IRS has been cracking down on art donation schemes for years. They have special rules for donations over $5,000 and even stricter ones for donations over $500,000 - including requiring a qualified appraisal and attaching a complete appraisal report to the tax return. I wonder if the Green family's donations have been scrutinized under these rules? The IRS Art Appraisal Services unit specifically looks at high-value art and artifact donations because of the potential for abuse.
Chloe Harris
ā¢Good point. I read somewhere that donations of art/artifacts over $50k can trigger automatic review by the IRS Art Advisory Panel, which is made up of outside experts who determine if the claimed value is reasonable. I wonder if these donations went through that process?
CosmicCadet
ā¢You're correct about the Art Advisory Panel - they automatically review any artwork valued at $50,000 or more per item that's donated. For very high-value donations (which these certainly were), the Panel brings in outside experts in the specific type of artifact to evaluate the appraisals. Additionally, when there's a related-party transaction like this (same family owning both the business and the museum), the IRS applies extra scrutiny. They look for what's called "private benefit" - where the charitable donation primarily benefits the donor rather than serving a true charitable purpose. The fact that the Green family controls both entities would definitely raise flags in an IRS review, particularly with the 3x valuation pattern they apparently seek.
I'm surprised nobody mentioned Form 8282 "Donee Information Return" yet. If the museum sold or disposed of the donated property within 3 years, they would have been required to file this form reporting the sale price back to the IRS. This form is specifically designed to catch inflated appraisals - if someone donates something claiming it's worth $10 million but the receiving organization turns around and sells it for $2 million, the IRS gets notified of the discrepancy. In this case though, since the museum kept the items (until they had to be returned), this reporting requirement probably wouldn't have been triggered.
That's a good point about Form 8282. But I think there's another form at play here too - the museum would have had to file Form 8283 with their original appraisal information. That form requires signatures from both the donor AND a responsible person at the receiving organization AND the appraiser. So everyone involved is essentially certifying the claimed value. If the items later turn out to be stolen, I wonder if that exposes all three parties to potential penalties for filing false information?
Ella Lewis
ā¢@Anastasia Popova You raise an excellent point about Form 8283 and the multiple party signatures. However, penalties for false "information typically" require intent or gross negligence. If the parties genuinely believed the items were legitimate based on reasonable due diligence at the time, they might not face penalties even if the items later proved to be stolen. The IRS would likely focus more on whether proper appraisal procedures were followed and if the claimed values were supportable, rather than penalizing parties who were unknowingly deceived about provenance. That said, the IRS does expect donors and receiving organizations to exercise reasonable care in verifying authenticity, especially for high-value artifacts from regions known for trafficking issues. The bigger exposure is probably the recapture of tax benefits rather than fraud penalties, unless there s'evidence that any party knew or should have known about the stolen nature of the items.
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Luca Ferrari
Has anyone mentioned head of household status yet? That's what you'd probably be filing as now with kids and an unmarried partner. When comparing tax benefits of marriage, make sure you're comparing married filing jointly against head of household (not single), which already gives you some benefits. The marriage benefit might be smaller than if you were filing as single.
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Nia Davis
ā¢This is a really good point. I was head of household for years before getting married, and while marriage did save us money, it wasn't as dramatic as I expected. The tax brackets for HOH are already better than single.
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Emma Wilson
Great question! As someone who went through a similar situation, I can confirm there are definitely tax benefits to getting married when one spouse has no income. One thing I'd add to the excellent points already made - make sure you also consider the timing of when you get married. If you get married by December 31st, you're considered married for the entire tax year for IRS purposes. So if you're planning to tie the knot anyway, doing it before year-end could maximize your 2025 tax savings. Also, with three kids, you'll want to look into how the Child and Dependent Care Credit might change. If your girlfriend ever decides to work part-time or go back to work full-time, being married could affect how much you can claim for childcare expenses. The spousal IRA benefit mentioned earlier is huge too - that's potentially $7,000 more you can save for retirement while getting tax benefits. With 15 years together and three kids, it sounds like you're already a family in every way that matters. The tax benefits could just be the cherry on top of making it official!
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