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Ask the community...

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Paolo Ricci

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Had the EXACT same issue last tax season! šŸ˜‚ My wife's middle name was listed on her SSN card but I only used her middle initial on our return. Rejected THREE times before I figured it out. The stupid part? We'd been filing the same way for 4 years with no problems! Apparently the IRS updated their matching systems in 2023 to be more strict. Fixed it by using her full middle name and boom - accepted within 24 hours. Hope this helps with your moving plans!

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Honorah King

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I went through this nightmare last year and it was absolutely maddening! The key thing that saved me was requesting my wife's Social Security Statement online at ssa.gov - it shows EXACTLY how her name appears in their system. In my case, her name had a hyphen that we'd been leaving off for years, but the IRS suddenly started enforcing exact matches in 2023. Given your April 30th deadline, I'd also suggest paper filing as a backup plan. Yes, it takes longer to process, but at least you'll have officially filed by the deadline if the electronic version keeps getting rejected. You can always amend later once the name issue is resolved. Also, double-check that your wife hasn't had any recent credit monitoring alerts or identity verification requests from the IRS - sometimes those can trigger additional security flags that cause these matching errors. The whole situation is incredibly stressful when you're trying to coordinate a move, but you'll get through this!

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Anna Stewart

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That's a fantastic study plan revision, Emma! It sounds like you've really taken the advice to heart and created a comprehensive approach. One additional tip I'd suggest - since you mentioned you're juggling this with family life, consider setting up a study tracking spreadsheet or app to monitor your progress across all these different methods. It helps you see which areas need more attention and keeps you motivated when you can visually see your improvement. Also, since you're scheduled for January 5th, make sure to take a full-length practice exam under timed conditions about 2-3 weeks before your test date. This will help you identify any remaining weak spots and get comfortable with the exam format and timing. The real exam can feel quite different from doing scattered practice questions. Best of luck with your EA journey - your dedication and willingness to adapt your approach based on feedback shows you're going to do great!

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Great advice about the practice exam timing, Anna! I'm new to this community but have been lurking and reading everyone's tips. Just wanted to add that when you do take that full-length practice exam, try to simulate the actual testing conditions as closely as possible - same time of day, same room setup if possible, and definitely turn off your phone. I learned this the hard way when I took my first practice test at home with all the usual distractions and then felt completely thrown off by the quiet testing center environment. The adjustment was harder than I expected! Emma, your revised plan looks amazing - you're definitely setting yourself up for success.

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Amina Diop

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Welcome to the community, Emma! Your study plan sounds really solid, especially with the deadline motivation of having your exam scheduled for January 5th. One thing I'd add to all the excellent advice you've received - consider creating a "mistake log" as you work through practice questions. Write down not just what you got wrong, but WHY you got it wrong (misread the question, didn't know the rule, calculation error, etc.). This helped me identify patterns in my mistakes that I could then specifically address. Also, since you're multitasking with the audio content while with your kids, you might want to designate certain "focus topics" for those listening sessions vs. others. I found that simpler review material worked better during multitasking time, while I needed full concentration for complex topics like depreciation rules or partnership taxation. The fact that you're already thinking strategically about your approach and willing to adjust based on feedback tells me you're going to do great. The EA exam is challenging but very passable with the right preparation. Keep us posted on how your studying goes!

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Can I qualify for IRC Section 1202 QSBS exclusion for my tech company sale after reorganization from LLC to C Corp?

I've been searching everywhere for information and am completely lost. I even called the IRS directly but was told this is an "advanced question" they couldn't answer. Here's my situation with Section 1202 (Qualified Small Business Stock): - Started a tech company with 2 co-founders back in 2011 as an LLC - In 2013 we reorganized as an S Corp - In October 2018 we converted to a C Corporation (had to call Delaware corporate division today because one co-founder wouldn't share the documentation) - In August 2023 we sold the company, but my co-founders kept me in the dark about the sale details until I was basically handed documents to sign We had no idea about Section 1202 at the time of sale - I just discovered it yesterday while my wife was working on our taxes with TurboTax. I've held these shares since we founded in 2011 - they were original founder shares, not purchased. Is there any possibility I could qualify for the Section 1202 QSBS exemption on my proceeds from the company sale? I was prepared to pay the full tax amount and honestly just relieved to be done with one difficult co-founder. But now learning about 1202, it's devastating to think I might have missed out on a huge tax break by just a couple months! Our company definitely qualified financially as a small business under the asset test. Does anyone have experience with Section 1202 in situations like this with company reorganizations? Any chance I'm eligible?

Slightly different perspective - have you checked if you might qualify for the reduced 50% exclusion rather than the 100% exclusion? The rules vary based on when the stock was acquired as C corp shares. For C corp shares acquired after August 10, 1993 but before February 18, 2009, you can exclude 50% of the gain. For shares acquired after February 18, 2009 and before September 28, 2010, you can exclude 75%. And for shares acquired after September 28, 2010, you can exclude 100%. But this all depends on when the shares were acquired as C corp shares, which in your case sounds like October 2018, so you'd be in the 100% category if you met the holding period.

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Emma Davis

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This is a good point, but the exclusion percentages only matter if OP meets the 5-year holding requirement first, which seems to be the main issue here. Being 2 months short of 5 years means they likely can't access any of the exclusion percentages.

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I'm really sorry to hear about your situation - being just two months short of the 5-year requirement is incredibly frustrating, especially when you've been with the company since its founding. While the other commenters are correct about the general rule that C-Corp holding periods don't "tack" from previous entity types, there might be one avenue worth exploring given your specific timeline. Since your S-Corp to C-Corp conversion happened in October 2018, you should definitely investigate whether this qualified as a tax-free reorganization under Section 368 of the Internal Revenue Code. If the conversion was properly structured as a Section 368 reorganization (which many S-Corp to C-Corp conversions are), there's potentially an argument for holding period tacking under certain circumstances. This is an extremely technical area of tax law where the specific documentation and structure of your conversion matters enormously. Given the potential tax savings at stake, I'd strongly recommend consulting with a tax attorney who specializes specifically in Section 1202 and corporate reorganizations - not just a general CPA. You'll need someone who can review your conversion documents, operating agreements, and any legal opinions from 2018 to determine if there's any path forward. The fact that you were kept in the dark about sale details is also concerning from a fiduciary duty standpoint, but that's a separate issue. For now, focus on gathering all your corporate documents from the 2018 conversion and get specialized legal advice before your filing deadline.

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This is exactly the kind of detailed advice I was hoping for. You're right that being kept out of the sale discussions was problematic on multiple levels, but I need to focus on the tax implications first since the filing deadline is approaching. I'm going to dig through all the 2018 conversion paperwork this weekend. My co-founder who handled the legal work has been difficult to work with, but I think I can get the documents from our corporate attorney directly. Do you happen to know what specific language or provisions I should be looking for in the documents that would indicate it was structured as a Section 368 reorganization? Also, given how specialized this area is, do you have any recommendations for finding attorneys who specifically handle Section 1202 cases? Most of the tax attorneys I've found seem to focus on more general corporate tax issues.

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The Boss

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We did this exact same thing for years! My boyfriend and I owned a house together, paid from a joint account, but his income was much higher so he itemized while I took the standard deduction. He claimed 100% of the mortgage interest and property taxes, and we never had any issues with the IRS. Make sure your gf keeps a copy of the 1098 showing both your names but her SSN. That's really all the documentation needed since her SSN is the only one on the form anyway.

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Mason Kaczka

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That's really reassuring to hear! Did you ever get any questions from the IRS about it? And did you do anything special when filing to explain the situation?

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The Boss

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Never got a single question from the IRS in the 5 years we did this. Honestly, I think it's because the 1098 had his SSN on it, so the IRS computer system was already "expecting" him to report the full amount. We didn't do anything special when filing - he just entered the full amount from the 1098 on his Schedule A. We kept copies of our bank statements showing joint contributions to the mortgage payments just in case, but never needed them. The key is that between the two of you, you're not deducting more than 100% of what was actually paid.

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This is actually a pretty straightforward situation! Since you're unmarried, the IRS doesn't require you to split deductions proportionally like married couples filing jointly would. The key principle is that whoever actually paid the expenses can claim the deduction. Since you're both paying from a joint account that you both contribute to, either of you could technically claim these deductions. Given that you're taking the standard deduction anyway and she benefits from itemizing, having her claim 100% makes perfect financial sense. A few important points to keep in mind: - Make sure the total claimed between both returns doesn't exceed 100% of what was actually paid - Keep good records showing you both contribute to the joint account used for mortgage payments - Since her SSN is on the 1098, the IRS system is already expecting her to report this income, which actually makes this cleaner I'd recommend she keep a copy of the 1098 showing both names and her bank statements demonstrating joint contributions to the mortgage payments, just for documentation purposes. This is a completely legitimate tax strategy for unmarried joint homeowners!

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Amina Bah

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My partner and I did this 3 years ago! One tip: consider putting only one person on the mortgage but both on the deed if your bank allows it. That way, only one person claims all the interest but both have ownership. We did this bc my credit score was way better so I got the loan alone (better rate!) but we're both on the deed. The person not on the mortgage can just transfer their share of the payment to the mortgage holder, who then makes the full payment and claims 100% of the deduction. Simplifies taxes a lot! But u need to trust each other obvs.

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Isn't that technically mortgage fraud? I thought the person claiming the deduction has to be legally responsible for the debt. If only one person is on the mortgage, can they really claim 100% even if the other person is paying half?

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CosmicCowboy

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Just a warning - I tried doing this exact arrangement and it backfired on me. When my partner and I split, I had no legal right to the mortgage interest deductions despite paying half the mortgage for years. Also created huge issues when we sold since I was on the deed but not the mortgage. Would not recommend.

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Ava Garcia

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Great question! I went through this exact situation two years ago when my partner and I bought our first home. Here's what I learned from working with both a tax professional and mortgage lender: Since you're both on the mortgage and splitting payments 50/50, you can each deduct your proportional share of the mortgage interest on your individual tax returns. Keep detailed records of who pays what - bank statements, cancelled checks, or electronic transfer records showing each person's contribution. One key thing to watch out for: the mortgage lender will send ONE Form 1098 (mortgage interest statement) to whoever is listed as the primary borrower. You'll need to coordinate to ensure you both get the information needed for your tax returns. Some couples scan and share the 1098, others request the lender send copies to both parties. Also, don't forget about property taxes! If you're splitting those 50/50 as well, you can each deduct your portion of property taxes paid, which also goes on Schedule A. Given your combined income of $180k and a $520k mortgage, you'll likely have enough deductions to make itemizing worthwhile. The mortgage interest alone in your first few years will probably exceed the standard deduction threshold. One last tip: consider having a tax pro review your first year's return to make sure you're handling everything correctly. It's worth the cost to get it right from the start!

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This is really helpful advice! Quick question about the Form 1098 - if the lender only sends it to the primary borrower, do we need to do anything special to make sure the IRS knows we're each claiming our portion? Or is it enough that we each report our share on our individual Schedule A forms? I want to make sure we don't accidentally trigger any red flags by both claiming parts of the same 1098.

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