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Just a practical tip from someone who went through tax court for a similar issue - request your cell phone records from 2021! They show your location data throughout the year and can be powerful evidence that you were in the same location as your children. Also, if you have a co-parenting app or calendar that tracks custody time, get a complete export of that data. Make sure to create a simple calendar visual that clearly shows the days your children were with you - judges appreciate easy-to-understand visuals rather than just stacks of documents. I created a color-coded calendar that made it immediately obvious I had the kids more than 6 months.
That calendar visual idea is brilliant! Did you just use like a regular wall calendar and highlight days, or did you make something digital? I'm not very tech-savvy but could probably figure out a basic spreadsheet if that would look more professional.
I actually did both! I created a digital calendar in Excel where I color-coded days (green for days with me, yellow for days with their mom), and then printed it out. I also made a simple count at the bottom showing the total days for each month and the running total for the year. The judge really appreciated having that visual. Even a hand-colored paper calendar would work fine - the key is making it easy for the judge to see at a glance that you met the six-month requirement. Just make sure you can back up each colored day with some form of evidence. I organized my evidence by month in a binder, so when the judge questioned a particular period, I could immediately turn to that section and show the supporting documentation.
Don't forget about financial evidence! Bank statements showing regular purchases at grocery stores, children's clothing stores, and restaurants near your home can help establish a pattern consistent with having children living with you. Also, get a record of any child support payments you made or received - they help establish the formal custody arrangement. If your children participated in any activities (sports, music lessons, etc.), get attendance records and receipts for those as well. Did you claim your children on your health insurance? Get documentation from your insurance company showing they were covered under your plan in 2021.
This is all good advice but keep in mind the IRS isn't just looking for evidence you SUPPORTED the kids financially - they specifically need proof the kids LIVED with you for more than half the year. I've seen people bring tons of payment receipts but still lose because they couldn't prove physical residency.
Is there any chance your employer qualifies for FMLA? The cutoff is 50 employees within 75 miles, but sometimes small businesses are actually part of larger corporate structures that might push them over the threshold. Also, have you looked into whether your state has any pregnancy accommodation laws? Some states have protections that kick in at lower employee counts than FMLA. Might be worth checking what your state offers specifically.
I'm sure we don't qualify for FMLA - we're truly a small independent business with just 12 employees total. I did check into my state's laws and unfortunately we're in a state with minimal protections beyond the federal requirements. I'm going to look into the temporary disability option that a few people mentioned. I had no idea that might be available to me! And I'm definitely not going to file for unemployment fraudulently. After reading everyone's comments, I can see that's a terrible idea that could come back to haunt both me and my employer.
Your employer might not understand that unemployment agencies often cross-check data with the IRS. When you claim a new dependent (your baby) with a birthdate that matches your "layoff" period, it creates an obvious red flag. I process payroll for a small business and this kind of stuff gets caught more often than people think.
This is so true. My sister works for our state's unemployment department and they absolutely compare birth records with unemployment claims. They also check social media sometimes. Someone at her office caught a claimant posting about their new baby on Facebook during the exact period they claimed to be "laid off" and actively seeking work.
Don't forget you can also deduct your losses up to the amount of your winnings if you itemize deductions instead of taking the standard deduction. So if you won $195 but lost $100 getting there, you'd only owe taxes on $95 of gambling income. Just make sure you have records of both the wins AND losses!
But isn't itemizing only worth it if all your deductions add up to more than the standard deduction? That's like $13,000+ for a single person. Seems like you'd need a lot more than some gambling losses to make itemizing worthwhile.
That's absolutely right. Itemizing only makes sense if your total deductions (including gambling losses, mortgage interest, certain state taxes, charitable contributions, etc.) exceed the standard deduction amount. For 2025, the standard deduction is projected to be around $13,850 for single filers. So unless you have significant other deductions, tracking gambling losses probably won't provide a tax benefit if your gambling activity is minimal like the OP's situation.
For small amounts like $195, most casual bettors just don't report it. Is it technically required? Yes. Will anything happen if you don't? Almost certainly not. The betting site won't report it to the IRS without hitting those W-2G thresholds others mentioned.
I wouldn't recommend this approach. Even small unreported income can cause issues if you're ever audited for other reasons. Better to report everything and stay clean.
About those 529 plans - while they don't give federal tax deductions, check if your state offers tax benefits! I live in NY and we get a state tax deduction up to $5K per year per beneficiary ($10K for married filing jointly). Made a huge difference on our state taxes.
This! I'm in Virginia and we get a $4,000 deduction per account on our state taxes. Definitely check your specific state rules - some states like Indiana even offer tax credits instead of deductions which are even better.
Exactly right! State benefits vary hugely - Pennsylvania and Montana have unlimited deductions for contributions, while states like Colorado, New Mexico, and others offer deductions up to the annual gift tax exclusion amount. Some states require you to contribute to their specific 529 plan to get the benefit, while others (like Arizona and Kansas) give you the deduction regardless of which state's plan you use. I'd recommend calling your state tax department directly to confirm what's available. The tax savings might not be as big as federal deductions, but they definitely add up over time, especially if you're contributing for multiple children.
For your property purchase idea, I did something similar buying a rental property. But don't just think about the mortgage interest deduction - consider the overall return. If you buy a $130k property with 20% down, your mortgage interest might only be $5-6k the first year, saving you maybe $1,300 in taxes if you're in the 22% bracket. But you could potentially also depreciate the property (except for the land portion), deduct property taxes, maintenance, insurance, etc. Plus hopefully the property appreciates in value and generates rental income. That's where the real benefit comes from. Don't buy property JUST for tax benefits - it needs to make sense as an overall investment.
Jace Caspullo
Just a practical tip from someone who's been in your shoes - with your income levels and having a child, you might actually get a refund rather than owing money. The Child Tax Credit is currently $2,000 per qualifying child, which can significantly offset your tax liability. Instead of focusing on allowances (which aren't even used anymore), I'd recommend having a small additional amount withheld from each paycheck if you're worried. Even just $20 extra per paycheck between the two of you would give you a nice cushion against owing anything.
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Melody Miles
ā¢So does the Child Tax Credit mean you get $2,000 back regardless of what you owe? Like if I owed $500 in taxes would I still get $1,500 back? I'm confused about how credits work vs. deductions.
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Jace Caspullo
ā¢The Child Tax Credit reduces your tax liability dollar-for-dollar, up to $2,000 per qualifying child. It's different from a deduction, which only reduces your taxable income. For example, if you would owe $3,000 in taxes without the credit, the Child Tax Credit would reduce that to $1,000. If you would only owe $1,500 in taxes, the credit would reduce your liability to zero, and you'd potentially get some of the remaining credit as a refund (up to $1,400 per child is refundable). The refundable portion means you can receive it even if you don't owe any tax.
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Nathaniel Mikhaylov
Has anyone else noticed that OP mentioned allowances but doesn't realize the W-4 form changed years ago? My company finally updated their system last year and it was so confusing to switch over.
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Eva St. Cyr
ā¢Yeah but some payroll systems and local forms still use allowances terminology. My company's internal system still asks for "allowances" even though they translate it to the new system behind the scenes. Super confusing for everyone.
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Nathaniel Mikhaylov
ā¢Good point! I didn't consider that some employers might still be using the old terminology internally. That makes the situation much more confusing for employees trying to figure out their withholding. Seems like a lot of companies have outdated systems that don't match current tax forms.
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