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Look, I'm gonna give you the real talk that your "friend" needs to hear. I didn't file my handyman business taxes for 2019. Thought I could just ignore it since it was just a side gig. BIG mistake. The IRS sent me increasingly scary notices, then hit me with penalties and interest that nearly DOUBLED what I originally owed. Ended up paying way more than if I'd just filed on time. Tell your friend to just get it done. Even a messy, imperfect tax return is infinitely better than no return at all. If they really can't figure it out, spend a few hundred on a tax pro - it'll be cheaper than the penalties in the long run.

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Nina Chan

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How long did it take before the IRS contacted you about the missing return?

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They sent the first notice about 8 months after the filing deadline. It was just a letter asking why I hadn't filed. Then about 2 months later, I got a more serious notice. By the third notice (around the 14-month mark), they had calculated what they thought I owed based on reported income from clients who sent 1099s, but without ANY of my business deductions. That's when things got really expensive because their calculation was WAY higher than what I would have actually owed if I'd filed properly with all my legitimate expenses. Then they started adding all the penalties and interest on top of that inflated amount.

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Ruby Knight

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Wondering if anyone knows how this would affect future W-2 employment? If the friend doesn't file for the sole proprietorship but then starts filing normally with their new W-2 job next year, will that trigger the IRS to look backward?

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Yes, it absolutely could. The IRS systems are designed to flag discrepancies and pattern changes in filing history. Going from non-filing to suddenly filing with W-2 income can trigger a review of prior years, especially if there's a business license on record that never had tax returns filed.

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Isaiah Cross

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22 Just a quick tip from experience - John Hancock's website is terrible for finding tax documents. If you did take a distribution and need a 1099-R, they might have it buried under "Statements & Documents" and then "Tax Forms" but sometimes they put it in a separate section entirely. Their search function is worthless too. You might need to call their customer service directly if you can't find what you're looking for.

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Isaiah Cross

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1 Thanks for this! I actually did take a small hardship withdrawal back in August that I completely forgot about! I'll check that section of the website. If they did send a 1099-R for that distribution but I can't find it online, how long do you think it would take to get a replacement?

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Isaiah Cross

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22 If you took a hardship withdrawal, you will definitely get a 1099-R and it's important to include it on your tax return. Those forms should be available by January 31st. If you can't find it online, call John Hancock directly - they can usually email you a replacement copy immediately. If for some reason they say they have to mail it, it typically takes 7-10 business days to arrive. But honestly, with most providers these days, they can send an electronic copy right away if you speak to the right department.

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Isaiah Cross

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16 Am I the only one who finds all these different tax forms completely overwhelming? I never know what I actually need and what I don't. I'm always afraid I'm going to miss something important and get audited.

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Isaiah Cross

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10 You're definitely not alone! I started using TaxAct last year and it actually walks you through everything step by step and asks all the right questions to make sure you're not missing anything. Way less stressful than trying to figure it all out myself.

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One thing to watch out for with the AOTC - make sure your cousin is actually eligible based on income! The credit starts phasing out at $80,000 modified AGI for single filers ($160,000 for married filing jointly) and goes away completely at $90,000 ($180,000 for MFJ). Also, don't forget that 40% of the AOTC can be refundable (up to $1,000), which is great for students who don't have much tax liability. That's a huge advantage over the Lifetime Learning Credit.

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Thanks for bringing that up! My cousin only made about $15,200 from his part-time job last year, so I don't think the income limits will be an issue. The refundable portion is great news though - that extra $1,000 would help him a lot with next semester's expenses! Question though - does he need to be claimed as my dependent to get the AOTC, or can he file independently and claim it himself?

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No, he doesn't need to be your dependent to claim the AOTC himself. If he's not a dependent on anyone's return, he can claim his own AOTC on his tax return based on qualified education expenses that he paid. However, if someone else (like his parents) claims him as a dependent, then they would be the ones eligible to claim the AOTC based on education expenses they paid. The student can't claim education credits for expenses that were paid by others or covered by tax-free scholarships. In your case, if he's filing his own return and paid his own education expenses (or took out loans in his name), he should claim the credit himself. If his parents paid some expenses, they might be able to claim a portion of the credit if they claim him as a dependent.

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Ravi Gupta

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I work in my university's financial aid office, and I see students miss out on the AOTC all the time! Make sure you keep receipts for ALL required materials for courses - not just textbooks. Lab supplies, special software, art materials, etc. can all qualify if they're required for courses. Also, if adjusting which expenses were covered by scholarships helps maximize the credit, you can do that! The IRS doesn't dictate which expenses scholarships must apply to first.

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GalacticGuru

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Wait really?? So if my scholarship was $5000 and I had $4000 in tuition and $3000 in room/board, I could choose to apply the scholarship to room/board first to maximize my qualified expenses for AOTC?

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Gavin King

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What software are you using for international forms? I found that switching from Lacerte to UltraTax made a huge difference for me with expatriate clients. The diagnostics for international reporting are much more comprehensive.

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Nathan Kim

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I second this. UltraTax has better international diagnostics, but CCH Axcess actually has the best guided worksheets for Form 5471 Schedule J and E calculations in my experience.

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Gavin King

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Thanks for mentioning CCH Axcess - I haven't tried their international modules yet. I still supplement UltraTax with manual Excel templates for some of the more complex PFIC calculations, especially when dealing with excess distributions from foreign mutual funds. The software's built-in calculations don't always capture all the nuances.

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I feel your pain! I nearly quit in my third season too. What saved me was finding a mentor who specialized in international tax. Have you tried looking for someone more senior who might be willing to review your work before it goes to the official reviewer? Also, standardize your approach. I created templates for client questionnaires specifically designed to catch international reporting triggers. For example, I have specific questions about signatory authority on foreign accounts (for FBAR/8938) and detailed ownership questions to catch potential CFCs and PFICs. Don't give up - it does get better!

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Quick question - is your ex-wife transferring the money directly to your loan servicer or giving it to you first? If she pays the educational institution directly, she might qualify for an educational exception to the gift tax limits, which would mean she wouldn't need to file a gift tax return at all, even though it's over the annual exclusion.

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ThunderBolt7

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I don't think that education exception applies to student LOANS though, right? I thought it only applies when paying tuition directly to the school for current education expenses, not for paying off existing loans after graduation.

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I know everyone's focusing on the gift tax aspect, but don't forget to check if your state has its own gift tax. Most states don't, but a few still do. Connecticut definitely has one, and a couple others might depending on your location. Just something else to keep in mind!

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