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Ask the community...

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Malia Ponder

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If u make under $12,950 in 2024, u might not even need to file a return at all if ur a dependent. But u should still file anyway to get any witholding back! And track all ur expenses, art supplies, software, part of ur internet bill, etc.

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Kyle Wallace

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This isn't completely accurate. Self-employed people need to file if they make $400 or more net income, even if they're dependents. The $12,950 threshold is for regular W-2 income, not self-employment income.

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Ana Rusula

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Great thread! As someone who went through this exact situation a few years ago, I wanted to add a few things that really helped me when I was starting out as a freelance digital artist. First, definitely set up a separate bank account for your business income and expenses if you haven't already. It makes tracking everything so much easier come tax time, and the IRS loves clean records if you ever get audited. Second, don't forget about state income tax requirements! Even though your state doesn't charge sales tax on digital goods, you'll still likely owe state income tax on your freelance earnings. Each state has different thresholds and rules. Also, since you're tracking everything in a spreadsheet already, consider categorizing your expenses more specifically - things like "software subscriptions," "equipment," "professional development," etc. This will make filling out Schedule C much smoother and help you spot deduction opportunities you might miss otherwise. One last tip: if you end up owing more than $1,000 in taxes when you file, you'll definitely want to start making those quarterly estimated payments for next year to avoid penalties. The IRS doesn't like waiting until April to get their money! You're being really smart about getting ahead of this. Most freelancers I know (myself included) learned this stuff the hard way after making mistakes.

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Sophie Duck

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This is such helpful advice! I'm actually just getting started with freelance work myself and had no idea about the separate bank account thing. That makes so much sense for keeping everything organized. Quick question - when you say "professional development" as a category, what kind of expenses would fall under that? Like online art courses or tutorials? And do those actually count as legitimate business deductions even if they're helping me improve skills I already use? Also really appreciate the heads up about the $1,000 threshold for quarterly payments. I was worried I'd have to start making estimated payments right away even with smaller amounts.

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Mei Lin

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Watch out for state estate or inheritance taxes too! Everyone's focused on federal, but depending on where your father-in-law lived, there might be state taxes to deal with that have much lower exemptions than federal. Connecticut, for example, has a lower estate tax exemption than the federal one.

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This is so true! My uncle's estate was under the federal exemption but got hit with a hefty state estate tax bill in Massachusetts. Their exemption is only $1 million, way less than the federal amount.

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Kolton Murphy

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This is such a complex situation, and I really appreciate everyone sharing their experiences and insights. As someone who works in estate planning, I want to emphasize a few key points that haven't been fully addressed: First, timing is absolutely critical here. The 9-month deadline for filing Form 706 (with possible 6-month extension) isn't just about taxes owed - it's about preserving options. Even if the marital deduction eliminates all estate tax, filing preserves the portability election AND starts the statute of limitations running on IRS challenges to asset valuations. Second, the trust structure really does determine everything. If this was a revocable trust, the assets are included in the estate for tax purposes but may still qualify for the marital deduction depending on how the trust is structured post-death. If it's an irrevocable trust created during lifetime, you need to determine if it was a completed gift (requiring gift tax analysis) or if your father-in-law retained powers that kept it in his estate. Third, don't overlook the generation-skipping transfer tax implications if the trust has provisions for grandchildren or other skip persons. This can create additional filing requirements and potential taxes even when estate tax is avoided through the marital deduction. I'd strongly recommend getting professional help given the $14.5 million estate size - the cost of proper planning and compliance is minimal compared to potential penalties or missed opportunities.

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Diego Rojas

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Thank you for this comprehensive breakdown - it really helps clarify the complexity of our situation. You mentioned the generation-skipping transfer tax, and that's something we haven't even considered yet. The trust does include provisions for our children (his grandchildren) to receive distributions under certain circumstances. How do we determine if this triggers GST tax requirements? Is this something that would be reported on Form 706 or does it require a separate filing? Given the size of the estate, I'm worried we might be missing other important deadlines or requirements.

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The "free" tax prep industry is such a scam. Most of these companies actively lobbied AGAINST the IRS creating its own free filing system for years. They make their interfaces deliberately confusing to upsell you on premium features. I switched to paper filing with the official IRS forms a few years ago and never looked back. Yes, there's a learning curve, but once you understand the basic forms, it's not that complicated for most people. Plus, you actually learn how taxes work instead of just plugging numbers into boxes without understanding why.

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Emma Garcia

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Doesn't paper filing take forever to process though? I heard the IRS is still working through a backlog from like two years ago.

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I've been dealing with this same frustration! Last year I got hit with a $25 amendment fee from TaxAct after they advertised "free filing." It's so misleading when they only mention the fees buried in the fine print. One thing that helped me was using the IRS's own Free File Fillable Forms for my amendment this year. It's completely free but you're basically filling out the raw Form 1040-X yourself without much guidance. The interface is pretty bare-bones but if you have your original return handy and the corrected information, it's manageable. The key is being extra careful since there's no error-checking like the commercial software. I printed out the IRS instructions for Form 1040-X and followed them step by step. Took me about 2 hours but saved me the $20+ fee. For next year, I'm planning to be more methodical about gathering ALL my tax documents before I start filing to avoid amendments altogether. Maybe make a checklist of all possible income sources from the previous year.

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That checklist idea is brilliant! I wish I had thought of that before filing. I'm definitely going to create one for next year with all the usual suspects - W-2s, 1099s from banks, any freelance work, investment accounts, etc. Maybe even set calendar reminders in January to check for documents that might come later in the filing season. It's so much easier to be thorough upfront than deal with amendment fees and the hassle of correcting everything later.

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Jade Santiago

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Has anyone tried Cash App taxes? They don't do advances but its completely free to file

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Caleb Stone

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Been using them since they were Credit Karma Tax. Super easy if you have a simple return!

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Daniel Price

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ur better off waiting for ur actual refund tbh. these advance loans are just another way for these companies to make $$ off poor people πŸ’…

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Vanessa Chang

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some of us dont have a choice tho... bills don't wait

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CosmicVoyager

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I literally just went through this last week! For Line 4 (tax liability), I just used my 2022 tax return and found the line that said "total tax" (I think it was line 24 on the 1040). For line 5, I added up all the federal taxes from my paystubs for 2023 (look for "Fed Withholding" or similar). Line 6 was just the difference, and for line 7, I paid about half of what I owed just to be safe.

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Ravi Kapoor

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But doesn't that mean you'll get charged interest and penalties on the unpaid portion? I thought you had to pay your full estimated tax by the deadline even with an extension?

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Ella Russell

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You're absolutely right to be concerned about this! An extension to file is NOT an extension to pay. If you owe money, interest and penalties will start accruing from the original due date (April 15th for most people) on any unpaid balance. The general rule is that you should pay at least 90% of what you owe by the deadline to avoid penalties. So if @CosmicVoyager only paid half, they might face penalties unless their withholding plus that payment equals at least 90% of their total tax liability. That said, if you can't pay the full amount, it's still better to pay what you can rather than nothing at all. The penalties and interest on a partial payment are less than on the full amount.

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StarStrider

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I completely feel your frustration! I was in the exact same boat last year - staring at Form 4868 like it was written in hieroglyphics. Here's what helped me understand it: Think of "tax liability" as your final grade on a test, and "payments" as all the homework points you already earned throughout the year. Line 4 is asking "what do you think your final tax grade will be?" and Line 5 is "how many homework points (tax payments) have you already earned?" Since you don't have your W-2 yet, here's a quick workaround: Look at your last paystub from December 2023. It should show your year-to-date federal tax withholding - that's your Line 5 number. For Line 4, if your income was similar to 2022, you can use last year's "total tax" from your 2022 return as a starting estimate. Don't stress too much about getting it perfect - the IRS knows these are estimates on extension forms. The key is making a reasonable good-faith effort. Once you get all your documents, you'll calculate the exact amounts on your actual tax return. Also, remember that filing an extension gives you until October to file your return, but if you owe money, you still need to pay by the original deadline to avoid interest charges. So it's better to overestimate a bit than underestimate!

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