Another option nobody's mentioned - if your 1099 work is through a single client or platform, you can sometimes ask them to withhold taxes for you. I do contract work and my main client withholds 22% federal tax on my payments. Not perfect but better than nothing and saves me from quarterly payment headaches.

I've been managing a similar mixed income situation for the past few years and learned some hard lessons. Here's what I wish I knew when I started: The key threshold you're looking for is owing $1,000 or more in tax after withholding and credits. But the real trap is the "safe harbor" rule - you need to pay either 90% of this year's tax OR 100% of last year's tax (110% if your AGI was over $150k) through withholding and/or quarterly payments. With your variable 1099 income ($800-$7,500/month), you'll likely cross the $1,000 threshold pretty quickly. The IRS doesn't care that your income is unpredictable - they expect payments throughout the year. Here's my suggestion: Keep some federal withholding on your W-2 (maybe 50-75% of what you normally would) and make quarterly payments only for the excess 1099 income. This hybrid approach gives you most of the interest benefits while reducing penalty risk. For comprehensive guidance, Publication 505 is actually pretty detailed once you get past the IRS-speak. The worksheets in there will help you calculate exactly what you need to pay quarterly. One last thing - if you do get hit with underpayment penalties, they're calculated from the due date of each quarter, so even earning 5.2% interest might not offset penalties if you're significantly short on payments.

Had the EXACT same issue last tax season! 😂 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!

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!

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!

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!

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.

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.

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.

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!