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  • DO post tips & tricks to help folks.
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Paolo Ricci

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Don't forget about charitable contributions! If you're looking for last-minute deductions, you can still make cash donations to qualified charities by the end of the year and claim them on your 2023 taxes. Just make sure you have proper documentation. Even if you take the standard deduction, you might qualify for a small deduction for cash donations under special rules. Also, if you have any unreimbursed medical expenses that exceed 7.5% of your AGI, gather those receipts. And check if your state has an income tax deduction for 529 plan contributions - some states allow this even if you make the contribution late!

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Amina Toure

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Wait, I thought the special rule for charitable donations when taking the standard deduction expired after 2021? Is that still available for 2023?

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Paolo Ricci

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You're absolutely right, and I apologize for my error. The special provision that allowed taxpayers to deduct charitable contributions while taking the standard deduction was temporary and has expired. For 2023, you would need to itemize deductions on Schedule A to claim charitable contributions. Thanks for the correction - it's important to have accurate information when making these last-minute tax decisions!

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For anyone rushing to make last-minute IRA contributions to reduce 2023 taxes, make sure your financial institution properly codes the contribution for tax year 2023! I made this mistake last year when I contributed in April - they defaulted it to the current calendar year. Had to get them to correct it, which was a hassle.

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Good point! Most online platforms have a dropdown or option to select which tax year the contribution is for, but it's easy to miss. I always take a screenshot of the confirmation page showing the tax year just to be safe.

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That's a smart approach with the screenshot! I've started doing something similar. When I make my contribution now, I actually call my financial institution afterward to verbally confirm they've recorded it for the correct tax year, then note the date, time and representative's name. It takes an extra few minutes but saves potential headaches later.

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Another option nobody mentioned - you can download your wage and income transcript directly from the IRS website, which might show your 1099 info even if the company hasn't sent it to you yet! Go to irs.gov and search for "Get Transcript Online." It doesn't always have everything right away, but it's worth checking. The transcript shows all information returns reported to the IRS under your SSN, including W-2s and 1099s. Saved me last year when a client claimed they mailed my 1099 but it never arrived.

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Thanks for this suggestion! I just tried accessing my transcript online but it looks like it only shows forms that have already been processed by the IRS. Since my client is late sending the 1099, it's not showing up there yet. But this is definitely good to know for the future or if I need to verify what's been reported under my SSN.

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Diego Chavez

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I'm a bookkeeper for several small businesses and just want to add - you absolutely do NOT need the physical 1099 form to file your taxes! Many of my clients panic about this. Here's what you need to do: 1. Add up all payments you received from the startup during 2024 2. Report the total on Schedule C as income 3. Deduct any legitimate business expenses 4. File your complete return with both W-2 and 1099 income TurboTax walks you through this really easily. The physical 1099 form is just an information document - the IRS actually gets their own copy. They care that you report ALL income, not that you have the paper form.

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NeonNebula

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What if the amount I calculate from my records is different from what eventually shows on the 1099 when they finally send it? Will that cause problems with the IRS?

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Luca Conti

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Just a heads up for anyone struggling with sales tax - the requirements are different in every state AND they change constantly. I got hit with a huge penalty because I didn't realize that once I hit $100,000 in sales in Michigan, I was supposed to start collecting sales tax immediately (I thought I could wait until the next quarter). Make sure you understand not just how to account for sales tax, but also when you're required to start collecting it in each state where you have customers. Economic nexus thresholds (the amount of sales that trigger the requirement to collect) vary from state to state.

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Nia Johnson

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Do you need to collect sales tax based on where your business is located or where your customers are? I ship to people all over the country and I'm so confused about this part.

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Luca Conti

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You need to collect based on where your customers are located, not where your business is. This is called "destination-based" taxation and most states use this approach. So if you're in Texas but shipping to a customer in California, you'd charge California sales tax (assuming you have nexus in California). Each state has different rules for when you establish "nexus" (the obligation to collect), but generally it's based on either physical presence (having inventory, employees, etc. in the state) or economic presence (selling over a certain dollar amount or number of transactions to customers in that state).

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CyberNinja

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For sales tax bookkeeping, I use a really simple system in my spreadsheets. I have columns for: - Total sale amount (what customer paid) - Sales tax collected - Net sale (pre-tax amount) Then I transfer the sales tax to a separate savings account each month so I don't accidentally spend it. When it's time to file my quarterly returns, the money is already set aside.

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Mateo Lopez

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I tried doing spreadsheets but it got so complicated with different tax rates in different counties and cities. What do you do when you have to calculate different rates for different customers?

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Yara Abboud

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One important thing to consider with the mark-to-market election is that it's irrevocable unless you get IRS permission to change it. Make sure you fully understand what you're getting into before making the election. For some traders it's amazing, for others it can actually increase your tax burden.

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PixelPioneer

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Does the election apply to all securities you trade or can you designate only certain accounts? I do both long-term investing and active trading but keep them in separate accounts.

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Yara Abboud

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The election applies to all your securities that are part of your trading business. The key is proper segregation. If you have legitimate investment accounts that are clearly separated from your trading accounts, you can keep those as capital assets subject to regular capital gains treatment. You'll need to clearly document this separation ahead of time and be consistent in how you treat those accounts. Many traders maintain separate accounts - one for long-term investments (capital asset treatment) and others for active trading (mark-to-market treatment).

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Don't forget you'll need to make quarterly estimated tax payments if you go the trader route! When I first started, I had a killer first quarter with huge profits, didn't make estimated payments, and got absolutely destroyed with penalties. The IRS doesn't play around with this.

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Paolo Rizzo

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Is there a specific form for the estimated payments or just the regular 1040-ES? And how do you calculate if your trading income varies wildly month to month?

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You use the regular 1040-ES for the payments. For wildly varying income, you have two options: you can either pay based on your actual income for each quarter (which requires more calculation but can match your cash flow better), or use the "safe harbor" provision by paying 100% of last year's tax liability (110% if your income was over $150,000). I personally track my trading P&L monthly and adjust my quarterly payments accordingly. It's more work but prevents overpayment when I have down quarters. Just make sure you're keeping detailed records of your calculation method in case of questions later.

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One thing nobody's mentioned yet - make sure you're aware that some credit card companies count tax payments as cash advances, not purchases! This happened to me last year and I got hit with cash advance fees AND didn't get points for the spending. Double-check with your specific credit card issuer before you do this. Most major cards like Chase, Amex, and Citi count tax payments as regular purchases, but store cards and some smaller banks might categorize them differently.

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Oh wow, that's really good to know! I hadn't thought about that. I have a Chase Sapphire card - do you know if they treat tax payments as regular purchases? And is there any way to confirm this before I make the payment?

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Chase Sapphire definitely treats tax payments as regular purchases! I've used my Chase cards for this exact purpose multiple times and always earned the points with no issues. You can confirm by either calling the number on the back of your card and asking directly, or check their terms and conditions. Most major card issuers also have this info in their FAQ sections online. Just search for "tax payments" or "government payments" in their help section.

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Just wanted to drop a quick reminder that while using credit cards for tax payments can be great for bonuses, don't forget that the processing fee is NOT tax deductible for personal tax payments. It's only deductible if you're paying business taxes like self-employment tax.

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Justin Trejo

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Are you 100% sure about this? I thought I read somewhere that credit card convenience fees could be deducted as a miscellaneous expense?

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