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I'm a tax preparer and I see this situation all the time. File your 2024 return on time no matter what! The systems for different tax years are separate, so a new return won't interfere with resolving the old ones. You can request an automatic extension until October if you need more time to gather documents, but remember that any taxes owed are still due by the April deadline. One thing to check: did you elect to apply any portion of previous refunds to this year's taxes? If so, that could complicate things since those credits might be in limbo. Make sure your 2024 return doesn't rely on carryover credits from those unprocessed returns.
What about amended returns? I'm in a similar situation but need to amend my 2023 return. Should I wait until my original 2023 return finishes processing before filing the amendment?
Yes, for amended returns you absolutely need to wait until the original return has been processed before filing the amendment. The IRS can't process an amendment to a return that hasn't been processed yet - it would just create more confusion in the system. If you file an amendment before the original return is processed, it will likely be rejected or get stuck in processing limbo. Wait until you can verify your original return has been processed (check your transcript or account online) before submitting Form 1040-X.
Has anyone tried requesting a Taxpayer Advocate? I had a similar issue last year and the local Taxpayer Advocate Service office was able to resolve it within 6 weeks after I'd been stuck for almost a year. You have to show that you're experiencing a financial hardship though, like facing eviction or utility shutoff, or that the IRS has made the same error repeatedly.
One option nobody mentioned is getting a current appraisal before you sell the rug. This establishes the true fair market value right now. If it's significantly less than what it was worth when you inherited it (which you'd need to establish with a retrospective appraisal), then you have documentation to support your claimed loss. Also remember losses on personal property generally aren't deductible UNLESS they were investment property. Since you mentioned you've been buying and selling on eBay for years, you might be able to make the case these were investment items rather than personal use items.
So does that mean I need to prove I bought the other collectibles as investments rather than for personal enjoyment? How exactly do I demonstrate that to the IRS? I never formally tracked anything as "investment" vs "personal" when I was buying stuff.
You would need to show evidence that suggests investment intent rather than personal use. Things that help establish this include: keeping detailed records of purchases and sales, maintaining an inventory system, researching market values before buying, having a dedicated space for your collection, and having a history of actually selling items for profit rather than just accumulating them. The IRS looks at factors like frequency of transactions, effort to improve marketability of items, and whether you depend on income from sales. You don't need formal designation documents, but consistency in how you've treated the items. Even documenting that you've been researching values and market trends can help establish investment intent.
Just want to add a quick warning - be careful with selling too many items on eBay or you might be considered a dealer rather than a collector, which changes the whole tax situation. The IRS looks at things like volume of sales, how often you sell, and whether you're making improvements to items before selling. If they decide you're a dealer, your profits become ordinary income instead of capital gains, which means potentially higher tax rates and also self-employment taxes.
I tried a bunch of different options after leaving my CPA and honestly ended up going back to him. The time I spent trying to manage everything with online services, fixing their mistakes, and chasing down answers probably cost me more than what I was "saving" in bookkeeping fees. One thing I did negotiate with my CPA was a monthly maintenance package instead of a big annual fee. I pay $325/month and he handles all my bookkeeping, quarterly estimates, and year-end tax prep. Maybe see if your previous CPA offers something similar?
$325 a month actually seems reasonable for everything you described. Does your CPA also help with tax planning throughout the year or just the compliance stuff? I'm trying to figure out if I'm overpaying at $450/month.
He does provide some tax planning, but it's fairly basic - mostly around estimated quarterly payments and year-end strategies like equipment purchases. We have two scheduled check-ins during the year specifically for tax planning. For more complex planning or when I have specific questions, I pay an additional hourly rate ($175/hr). So if you're getting comprehensive tax planning included in your $450, that actually might be a pretty good deal depending on the complexity of your business. My business is fairly straightforward though - single-member LLC with about $280K in revenue.
Has anyone tried using freelance bookkeepers on Upwork or Fiverr? I've been considering this route since it seems more affordable than going back to a full CPA firm.
Whatever you do, DON'T IGNORE THIS! I made that mistake and ended up with a tax lien that destroyed my credit and made it impossible to refinance my house. The IRS can also levy your bank accounts and garnish your wages if you don't set up some kind of arrangement. I'd recommend calling the IRS directly (if you can get through) and asking about the Fresh Start program. They've expanded it in recent years to help people with larger tax debts.
Do tax liens still show up on credit reports? I thought they changed that rule a few years ago.
You're right, and I should have been more clear. In 2018, the credit bureaus removed tax liens from credit reports as part of the National Consumer Assistance Plan. However, tax liens are still public records that can appear during background checks and mortgage applications. While they don't directly impact your credit score anymore, they definitely still affect your ability to get certain loans - especially mortgages. Lenders typically check for tax liens during underwriting. My situation happened before this change, but even today, a tax lien would prevent you from refinancing with most lenders until it's resolved.
Has anyone tried negotiating an Offer in Compromise? I've heard you can settle for pennies on the dollar but not sure if that's just marketing hype from those tax relief companies.
My brother got an OIC approved last year, but he had to prove serious financial hardship. They look at your assets, income, expenses - everything. He ended up settling about $45k for around $12k, but only because he had medical issues that prevented him from working full time and very few assets. If you have a decent income or any significant assets (home equity, retirement accounts, etc), you probably won't qualify. The IRS has a pre-qualifier tool on their website that's pretty accurate.
NebulaNova
If you're in this situation, definitely make sure you set aside money for taxes! I had a similar internship last year and was shocked by how much I owed at tax time since no taxes were withheld from my payments. You'll likely owe both income tax AND self-employment tax (which is about 15.3% on top of regular income tax).
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Diego Vargas
ā¢Oh no, I didn't realize I'd owe self-employment tax too! How much should I expect to pay roughly on $4,800? I haven't saved anything specifically for taxes since this is the first I'm hearing about this.
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NebulaNova
ā¢For $4,800 in 1099 income, you'll owe approximately $735 in self-employment tax alone (15.3% of your net earnings). Then you'll also owe your regular income tax on top of that, which depends on your tax bracket and other income you might have. If this is your only income for the year, some of it might be offset by your standard deduction, but you'll definitely still owe the self-employment portion. There's a small deduction for half of your self-employment tax, but you'll still need to prepare for a tax bill. Consider making an estimated tax payment if possible to avoid underpayment penalties.
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Mateo Hernandez
Has anyone actually used FreeTaxUSA for filing with a 1099-MISC? Is it actually free or do they make you upgrade for Schedule C like TurboTax did?
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Aisha Khan
ā¢I used FreeTaxUSA last year for a very similar situation (research stipend on 1099-MISC). Federal filing WITH Schedule C was completely free. State filing was $14.99, but that was it - no surprise upgrades or "premium" features needed for the 1099 income. Their interface for Schedule C was actually pretty straightforward too.
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