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Ask the community...

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  • DO NOT post call problems here - there is a support tab at the top for that :)

Amina Bah

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Has anyone run into issues with the hobby loss rule with something like D&D sessions? I'm worried the IRS might consider my similar side gig a hobby rather than a business.

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The key to avoiding the hobby loss rule is showing that you're running your D&D sessions as a business with the intent to make a profit. Keep good records, have separate business accounts, track all expenses properly, create a business plan, and be professional about how you operate. The IRS generally uses a "3 out of 5" guideline - if you show a profit in 3 out of 5 consecutive years, they typically consider it a legitimate business. Since OP mentioned they were "hit hard with taxes," it sounds like they're profitable, which helps their case significantly.

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Amina Bah

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That makes sense, thanks! I've been profitable 2 of the last 3 years, so I think I'm on the right track. I do have separate tracking for all my game master income and expenses, but I should probably open a dedicated bank account to make it even clearer.

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Oliver Becker

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I went through the S-Corp route with my freelance writing business and can confirm it saved me several thousand in self-employment taxes, BUT - and this is a big but - it only made sense once I was consistently making over $70k. The accounting and filing fees cost me about $1,200/year plus the extra time dealing with payroll. Stick with Schedule C for now, maximize your legitimate deductions, and revisit the business structure question when your income grows. The tax savings need to outweigh the additional costs and complications.

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JacksonHarris

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Here's a quick breakdown on self-employment tax that helped me: 1) You pay SE tax if net earnings are $400+ 2) The rate is 15.3% (12.4% Social Security + 2.9% Medicare) 3) Social Security part only applies to first $168,600 (for 2025) 4) You can deduct business expenses before calculating SE tax 5) On Schedule 1, you can deduct 50% of SE tax from gross income Don't forget to make quarterly estimated tax payments to avoid underpayment penalties!

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Ryan Andre

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Thanks for breaking this down! So for my $7,800, if I have say $1,200 in expenses for software, equipment etc., I'd pay the SE tax on $6,600, right? And should I be making quarterly payments even though I just started mid-year?

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JacksonHarris

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Yes, if you have $7,800 in income and $1,200 in legitimate business expenses, you'd pay SE tax on the $6,600 net profit. The SE tax would be about $1,010 (15.3% of $6,600). For quarterly payments, if this is your first year with self-employment income, you might qualify for an exception to the penalty. However, it's generally a good idea to start making them as soon as you realize you'll have tax liability. For the current year, you can catch up by making larger payments in the remaining quarters. The IRS website has a form (1040-ES) to help calculate your estimated payments.

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A tip nobody mentioned yet: keep track of your MILEAGE if you drive for your business! This is huge for self-employment deductions. Current rate is like 67 cents per mile for 2025 (check the exact amount) and it adds up fast. Also, dont forget about the QBI deduction (Qualified Business Income) which lets you deduct up to 20% of your business profit depending on your total income. This is separate from expenses and the SE tax deduction!

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Royal_GM_Mark

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The QBI deduction is amazing! But isn't there an income limit? I think I remember reading somewhere that it phases out if you make too much.

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Pregnant and my employer wants me to file for unemployment while on maternity leave - is this legal?

I'm in a bit of a dilemma with my small workplace (we only have 9 employees total). I'm currently pregnant and due in September. My boss is suggesting that when I go on maternity leave, I should file for unemployment and just state that I'm being "laid off" - without mentioning the pregnancy at all. They've assured me my position will be waiting for me when I return, and they'll give me a return date of December 15th. This seems sketchy to me. The company says they're suggesting this because our business has been down about 30% compared to last year, so they have a legitimate reason to temporarily "lay someone off" if unemployment officials ask questions. I went through something similar with my first child in 2023 - they initially told me to file for unemployment then too, but I was honest about having a baby and got denied. They ended up paying me $400 weekly for the 8 weeks I was gone. My biggest concern is that this feels like unemployment fraud. When I file taxes next year, I'd be showing unemployment benefits during the exact time I had a baby (whom I'll claim as a dependent). A couple friends I've talked to said this is definitely not legal. I really don't want to get my company in trouble as they've been supportive in other ways, but I also don't want to commit fraud. At the same time, I need some income during maternity leave. What should I do? Is what they're suggesting actually legal?

LilMama23

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I'm a manager (not in your company) and what your employer is suggesting is absolutely wrong and illegal. We once had an owner suggest something similar and our entire management team had to step in and explain the serious legal consequences. Here's what your company SHOULD be doing: - Providing FMLA paperwork if they have enough employees to qualify - Looking into short-term disability options - Checking if your state has paid family leave (many do now) - Being honest about what they can and cannot provide Asking you to lie on government forms is never okay, and shows they're trying to exploit the system rather than properly supporting their employees.

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Thank you for this perspective. Could you clarify about the FMLA part? I thought that only applied to companies with 50+ employees, and we only have 9 total. Are there similar protections for smaller businesses?

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LilMama23

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You're absolutely right about FMLA - it only applies to companies with 50+ employees, so your company is too small to be required to provide that protection. I should have been more clear. However, many states have enacted their own family leave laws that extend to smaller businesses. Depending on where you live, there might be state-specific protections even though you're not covered by federal FMLA. For example, some states require even small employers to provide job protection and/or paid leave. That's definitely worth looking into based on your specific location.

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Dmitri Volkov

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Wait, I'm confused about one thing - isn't your employer allowed to lay you off for business reasons? If their business really is down 30%, couldn't they legitimately lay you off and then you'd be eligible for unemployment? Or is it specifically because they're promising to hire you back that makes this fraud?

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The fraud part is the intentional misrepresentation. If they're specifically timing a "layoff" to coincide with maternity leave and have already promised to bring her back at a specific date, that's not a true layoff - it's a planned temporary absence that they're trying to disguise as a layoff to shift costs to the state. A legitimate layoff would be based solely on business needs, not timed specifically to coincide with a planned medical event, and wouldn't come with a guaranteed rehire date.

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TechNinja

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For what it's worth, I've been a homeowner for 10 years and still do my own taxes with TurboTax. Unless your situation is super complicated (like you're running a business from your new home or did some kind of unusual financing), the homeowner stuff isn't that hard. TurboTax walks you through it all with questions. The main things you'll deal with are: 1) Mortgage interest (from Form 1098 your lender sends) 2) Property taxes (also on Form 1098 usually) 3) If you paid points at closing (should be on Form 1098) If this is your only "complication" to your taxes, I personally wouldn't pay a preparer, but that's just me. I'd rather learn how it works myself.

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Dmitri Volkov

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Thanks for the perspective! Did you find that you were able to itemize deductions right away in your first partial year of homeownership? Or did it take a full year of mortgage interest before it made sense?

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TechNinja

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In my first partial year, I wasn't able to itemize because I only had about 4 months of mortgage interest which wasn't enough to exceed the standard deduction. I just took the standard deduction that first year. It wasn't until my first full calendar year of homeownership that itemizing made sense. But it's still worth running the numbers both ways in TurboTax (itemized vs standard) to see which gives you the better outcome. The software makes this comparison pretty easy.

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Don't forget to check if your state has any first-time homebuyer tax benefits! The federal credits have expired but many states still have them. I bought in Maryland and they had a program that saved me over $1,000 on my state taxes. TurboTax actually missed this when I tried to DIY, so I ended up going to H&R Block and they caught it.

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Paolo Bianchi

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What states still have good homebuyer tax breaks? I'm in Pennsylvania and when I asked my lender they said there weren't any tax breaks, just loan programs for first-time buyers.

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Yara Assad

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California still has some good ones! My friend just bought her first home and got a $10,000 credit through some state program. Definitely worth checking.

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Aaron Boston

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Another thing to consider: If you file separately, you'll lose several other tax benefits besides just the premium tax credit situation. You won't be able to claim: - Student loan interest deduction - Tuition and fees deduction - EIC in most cases - Child and dependent care credit - Some education credits Plus the standard deduction as a couple filing jointly is exactly 2x the single amount ($29,200 vs $14,600 for 2025), so there's no penalty there, but tax brackets for MFS aren't as favorable as MFJ. The $1,950 hit is painful but it's almost certainly your best option.

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Thank you, I hadn't even thought about all those other tax benefits that would be affected. We do have some student loan interest and education credits that would be impacted. Looks like filing jointly and taking the premium tax credit hit is even more clearly the right move than I initially thought.

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Aaron Boston

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Happy to help! Yeah, the MFS status really limits a lot of tax benefits, which is why it's rarely the optimal choice unless there are very specific circumstances. The premium tax credit "marriage penalty" is frustrating, but thankfully it's just a one-time adjustment you're dealing with. Next year you'll be able to plan your insurance coverage for the full year as a married couple and avoid this issue completely.

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Sophia Carter

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One more thought - have you considered if either of you could increase retirement contributions before the end of the year to lower your MAGI? If you're close to a threshold for the premium tax credit, sometimes putting an extra $1-2k into a traditional IRA or 401k can drop you into a lower income tier and reduce the amount you have to repay.

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Chloe Zhang

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This is really smart. I did this exact thing last year. Was going to owe $2,400 in premium tax credits after getting married, but maxed out my HSA ($3,850) and put another $2,000 in my traditional IRA. Dropped our MAGI just enough to reduce the repayment to only $800. Definitely worth looking into!

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I hadn't thought about this angle! We do have some room to make additional retirement contributions. I'll need to check exactly how close we are to the next MAGI threshold for the premium tax credits. Even if it just reduces the amount a bit, that's still a win since we'd be putting money into our retirement rather than just paying it to the IRS. Thanks for the suggestion!

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