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Don't forget you need to keep track of those payments to your helper for next year too! I recommend using an app like Quickbooks Self-Employed to track all your income and expenses. It makes it super easy to categorize expenses and you can even take photos of receipts. At tax time, you just send the report to your accountant or import into tax software.

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Vince Eh

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How expensive is Quickbooks Self-Employed? I'm trying to keep costs down since this side gig doesn't make a ton of money yet.

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The basic version runs about $15/month, but they often have sales for new users that can bring it down to around $7-8/month for the first year. They also have a free 30-day trial you can use to see if it works for you. I think it's worth the cost because it saves so much time and stress at tax time. You can also deduct the cost of the software itself as a business expense on your Schedule C, which helps offset the price a bit.

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im a dj who hires helpers sometimes and my accountant said make sure you have contracts with these people even if theyre friends. doesnt have to be fancy just something both sign saying they are contractors responsible for their own taxes. also keep a log of all events and payments!!! irs audited my friend who didnt have records and it was a nightmare for him.

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Vince Eh

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Thanks for the advice! I definitely need to get more organized with this. Do you just use a basic contract template you found online or did you have something professionally made?

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Chloe Harris

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@Vince Eh I just found a basic independent contractor template online and modified it for my DJ work. Nothing fancy - just covers the basics like payment terms, that they re'responsible for their own taxes, and what services they ll'provide. LegalZoom and Nolo have some decent free templates. The key is just having something in writing that shows you both understood this was a contractor relationship, not employment.

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Emma Garcia

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Another thing to consider - the rules for withdrawing from Roth IRAs with pre-tax portions are a bit complex. If your sister plans to withdraw before retirement age, she needs to understand the ordering rules. Generally, Roth IRA withdrawals come out in this order: 1. Regular contributions (after-tax) 2. Conversion contributions (taxable portion first, then non-taxable) 3. Earnings So those pre-tax portions would come out after her regular Roth contributions but before any earnings. This matters for determining if a withdrawal is subject to penalties. Honestly it's a headache to track this stuff, which is why I just converted my pre-tax portions when I did my rollover.

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Ava Kim

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Is there any way to specifically withdraw just the pre-tax money from a Roth? Like if you wanted to get that portion out first?

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Diego Fisher

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Unfortunately, no - you can't cherry-pick which specific funds to withdraw from a Roth IRA. The IRS ordering rules I mentioned are mandatory and apply automatically to any withdrawal. So you'd have to withdraw your regular contributions first, then the converted amounts (including those pre-tax portions), and finally any earnings. This is another reason why converting those pre-tax portions to full Roth status can simplify things - once converted, they become regular Roth funds without the special tracking requirements. Though of course you'd pay taxes on the conversion in the year you do it.

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PaulineW

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This is a great discussion! I went through something very similar with my 401k rollover from a non-profit job. The key thing that helped me was understanding that employer matching contributions are ALWAYS pre-tax, regardless of whether you're contributing to a traditional or Roth account. What really saved me headaches was calling my new IRA provider (in your case Vanguard) and asking them to walk through the tax implications of each option before making a decision. They can actually run scenarios showing exactly how much tax your sister would owe if she converts that $820 to full Roth status versus leaving it as-is. One thing I learned: if she's young and expects to be in a higher tax bracket later, paying taxes on that small amount now could save money long-term. But if she's closer to retirement or expects lower income later, it might make sense to leave it and pay taxes during withdrawal. The amount is small enough that either choice probably won't make a huge difference, but it's worth understanding the implications. Also, make sure she keeps documentation from the rollover showing which portions were pre-tax - you'll need that for future tax filings!

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Ethan Wilson

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This is really helpful advice! I'm dealing with a similar situation myself and hadn't thought about asking the IRA provider to run tax scenarios. That's a great idea. One question - when you say to keep documentation showing which portions were pre-tax, what specific documents should we be looking for? Is this something that shows up on the 1099-R from the rollover, or do we need to get separate paperwork from the old 403b provider? I want to make sure I'm not missing anything important for tax time next year.

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Just curious - what are you planning to replace it with? I'm shopping for a business vehicle and trying to figure out if it makes sense to go for something over 6000 lbs again for the tax benefits, or if those advantages aren't worth it anymore.

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Amina Diop

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Not OP, but I just went through this decision. The tax benefits for heavy SUVs are still significant if you genuinely need that type of vehicle. But remember, you're still spending real money to save on taxes. I ended up going with a more efficient vehicle because the operating costs were much lower, even though I got less depreciation up front.

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I'm actually going in the opposite direction - looking at the Ford Transit or similar work van. Better for my actual business needs and the depreciation benefits are still pretty good. I realized I'd rather have a vehicle that makes practical sense than one I chose primarily for tax benefits. The gas and maintenance savings alone will probably make up for any tax differences. Plus I won't hate driving it every day, which is a huge quality of life improvement!

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Sofia, I completely understand your frustration with that Range Rover! I've been in a similar situation with a heavy business vehicle that turned into more of a financial burden than benefit. One thing to consider that might help with the depreciation recapture burden - if your business has had a particularly good year, the recapture income (which gets taxed as ordinary income) might actually be beneficial for smoothing out your tax liability across years. Sometimes it's better to take the hit in a year when you can handle it rather than waiting and potentially facing it during a year with even higher income. Also, make sure you're tracking every single business expense related to the vehicle through the end - maintenance, insurance, registration fees, etc. These can help offset some of the recapture income. And if you're financing the replacement vehicle, the interest on that loan will be deductible for the business portion. The mental relief of getting rid of a vehicle you hate is worth a lot too. Sometimes the best financial decision isn't just about the numbers on paper!

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I'm dealing with a similar issue with my Ticketmaster 1099-K! Mine is off by about $2,200 and I've been trying to figure out where the discrepancy comes from. One thing that helped me was going through my Ticketmaster account settings and downloading the detailed transaction history (not just the summary). When I compared line by line, I found that some transactions were being counted twice - once when I originally bought tickets and again when I listed them for resale, even if they never sold. Also check if any refunded transactions are still being included in the gross amount. I had three events that got cancelled last year where I received full refunds, but those original purchase amounts were still showing up in my 1099-K total. It's frustrating that we have to do their accounting for them, but at least if you can identify the specific errors, you'll have solid documentation to include with your tax return. Keep pushing them for a corrected form though - you shouldn't have to explain away their mistakes to the IRS.

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Mei Liu

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This is really helpful! I hadn't thought to look at the detailed transaction history versus just the summary. The double-counting issue you mentioned makes a lot of sense - I definitely had listings that didn't sell but I wonder if those are still being included somehow. The cancelled events angle is interesting too. I had two concerts get postponed last year where I got refunds, but then rebought tickets when they rescheduled. If they're counting both the original purchase AND the new purchase, that could definitely explain some of the inflated numbers. Did you end up getting Ticketmaster to issue a corrected 1099-K, or did you just document everything for your tax return? I'm still deciding whether to keep fighting with them or just move forward with proper documentation of the actual amounts.

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Rhett Bowman

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This is such a widespread issue with Ticketmaster's 1099-K reporting! I've been dealing with tax prep for clients who resell tickets, and I see this problem constantly. A few additional things to check that might explain the discrepancy: 1) Service fees and taxes - Ticketmaster might be including their service fees and taxes in the gross amount, even though those weren't part of your actual sales proceeds. 2) Payment processing timing - If you had any sales in late December 2024 where the payment didn't process until early January 2025, those might be missing from your personal records but included on the 1099-K. 3) Promotional credits or vouchers - Sometimes platforms include the face value of tickets purchased with credits/vouchers rather than the actual cash amount you received. My advice: Don't wait for Ticketmaster to fix this. Document everything thoroughly and file with your correct numbers. The IRS understands these platforms have reporting issues. Include a reconciliation statement with your return showing your actual gross receipts versus the 1099-K amount, with line-by-line explanations for the differences you've identified. The key is having clean records that support your reported income. Better to file accurately than to report inflated income just because of a faulty 1099-K.

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Does anyone know if copies are ok or do they need originals?

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Diego Vargas

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Certified copies are fine for most docs except SS cards - those need to be original.

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Simon White

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Thanks for the heads up! As someone who's been doing their own taxes for years, this is really helpful to know. I was wondering why my usual tax prep place sent out that long list of documents to bring this year. It seemed excessive but makes total sense now with the IRS crackdown. Better to be over-prepared than deal with problems later. Appreciate you taking the time to explain this to everyone!

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PaulineW

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Totally agree! I'm new to this community but have been watching all the tax prep changes this year. It's crazy how much more documentation they're requiring now. I appreciate tax pros like @Chloe Anderson taking the time to explain this stuff - saves us all from showing up unprepared and wasting everyone s'time. Better to know what to expect going in!

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