FYI - one thing to watch out for with refinancing is if you do a cash-out refi, that can impact your capital gains calculation (though not the 2-year rule). The money you take out increases your basis adjustment, which could mean higher capital gains when you sell. For example, if you bought for $300k, did a cash-out refi and took $50k out, then sold for $400k, your capital gain wouldn't just be $100k... you'd need to adjust for that $50k you already took out.

Just wanted to chime in as someone who went through this exact scenario last year. I refinanced my home after owning it for about 20 months and was similarly worried about the capital gains exclusion timing. Can confirm that refinancing absolutely does not reset your ownership period - the IRS counts from your original purchase date when you first took title to the property. I ended up selling my home about 8 months after refinancing (so right at the 2-year mark from original purchase) and had no issues claiming the capital gains exclusion. One thing that might be helpful to keep in mind is documenting your primary residence period if you're close to the 2-year mark. I kept utility bills, voter registration, and other records showing continuous residence just to be safe, though I never needed them. The refinance actually helped in a way because all those documents clearly showed the same address throughout the process. Good luck with your timing - sounds like you'll hit your 2-year mark in about 6 months if my math is right!

Has anyone looked at how the IRS treats the "field of education" part? The regulations specifically mention education as an SSTB category, so I'm wondering if tutoring could fall under that regardless of the reputation/skill part.

I went through this exact same question last year and ended up consulting with a tax professional who specializes in small business deductions. What really helped clarify things for me was understanding that the IRS distinguishes between formal educational institutions and individual service providers. The key factor isn't just whether you're skilled or have credentials - it's whether your business model fundamentally depends on monetizing your personal reputation or fame. Most tutoring businesses are providing legitimate educational services based on subject matter expertise, which is different from the celebrity endorsement/appearance model that the SSTB "reputation or skill" category is targeting. In my case, I tutor high school students in calculus and physics. Even though I have advanced degrees and charge competitive rates, my business is structured around delivering actual educational outcomes rather than selling access to my personal brand. My tax professional confirmed this likely keeps me outside SSTB classification. The income threshold you mentioned ($155K) is definitely in the phase-out range, so getting this classification right is important for your deduction. If you're still unsure, it might be worth investing in a consultation with a tax professional who can review your specific business structure and marketing approach.

2 Has anyone used TIN matching with partnerships? We have an unusual situation where our LLC (taxed as partnership) needs to issue 1099s to several vendors, but we've heard that partnerships have different requirements for accessing the service.

I went through this exact process earlier this year for our consulting firm and wanted to share a few additional tips that might help: 1. Make sure you have your business banking information handy when applying - the IRS will ask for account details to verify your business identity during the e-services registration. 2. If you're planning to use the bulk upload feature (highly recommend for more than a few vendors), practice with the file format first. The IRS is very picky about the CSV layout and will reject your entire batch if even one row is formatted incorrectly. 3. Keep in mind that TIN Matching results are only valid for the calendar year you receive them. So if you verify TINs in December 2024, you'll need to re-verify them again for 2025 filings. 4. Pro tip: Run your TIN matching in early November if possible. This gives you time to reach out to vendors with mismatched information and get corrected W-9s before the 1099 filing deadline. The whole process definitely has a learning curve, but once you're set up it saves SO much time compared to dealing with IRS notices for incorrect TINs after the fact.

I'm an accountant and see this ALL THE TIME. Companies don't know how to properly handle non-employee reimbursements. Technically, the IRS doesn't have a specific reporting mechanism for reimbursing non-employees for expenses, which is why some companies default to the 1099-NEC. The safest approach is to report it on Schedule C if you're already self-employed, or as Other Income if you're not, and then offset it with the corresponding deduction. The IRS matching program will see the 1099-NEC was reported, preventing an automated notice, and the net tax effect will be zero.

This is such a frustrating situation that so many people run into! I went through something similar when a company reimbursed me for parking expenses during interviews and then sent me a 1099-NEC months later. The key thing to remember is that just because they issued a 1099-NEC doesn't mean you automatically owe taxes on it. Since this was a legitimate reimbursement at the standard IRS mileage rate (not payment for services), you can absolutely offset it. I'd recommend going the "Other Income" route on Schedule 1 that others have mentioned, since your husband isn't actually running a business. Report the $650 as other income, then claim the exact same $650 as a deduction for unreimbursed business expenses (which technically these were, since you incurred the expense first and were then reimbursed). This way you avoid any self-employment tax issues. Make sure to keep all your documentation - the mileage log, any emails about the reimbursement arrangement, and records showing it was calculated at the standard rate. The IRS will see the 1099-NEC was properly reported on your return, but the net tax impact will be zero.

Don't forget about appreciation! If you're still relatively young, consider that the assets you're planning to leave might grow significantly. $60M could become $100M+ over 10-20 years. Since the exemption amounts are likely to grow much more slowly (if at all), you might want to do some lifetime gifting to lock in today's exemptions. Even if you don't transfer the full amount now, moving appreciating assets out of your estate earlier can save a fortune in taxes. My parents did this with some startup stock that ended up growing 15x. By putting it in trusts for the grandkids early, they avoided millions in estate and GST taxes that would have been due if they'd waited.

This is such a helpful discussion! I'm dealing with similar estate planning questions and the interaction between these exemptions has been keeping me up at night. One thing I'd add is the importance of timing with the current exemption amounts. The current high exemptions ($12.92M per person in 2023) are set to sunset after 2025, potentially dropping back to around $6-7M per person. For estates like yours, this creates a real urgency to lock in planning strategies now. If you wait until after 2025, you might lose half of your combined exemption capacity. Even if Congress extends the higher exemptions, there's no guarantee. This is why so many high-net-worth families are accelerating their estate planning right now. Have you considered doing some lifetime gifting to your granddaughter now to use up your current exemptions while they're still available? You could potentially save millions in future taxes by acting before the exemptions potentially decrease. Just something to discuss with your estate attorney - the time value of using these exemptions now versus waiting could be enormous.