I'm dealing with a very similar situation and this thread has been incredibly helpful! I converted my primary residence to a rental in 2019 and just sold it this year. Like you, I qualify for the Section 121 exclusion on the gain, but I've taken about $15,000 in depreciation over the years. After reading through all these responses, it's clear that the depreciation recapture portion needs to be reported on Form 4797 even when the capital gain qualifies for exclusion. The Section 121 exclusion doesn't cover depreciation recapture - that's still taxable at up to 25%. I'm going to try that taxr.ai tool that was mentioned to double-check my situation before filing. It sounds like TurboTax struggles with these hybrid personal/business property sales, so getting a second opinion seems wise. Has anyone else used FreeTaxUSA for this type of transaction? The split reporting capability sounds like exactly what I need. Thanks everyone for sharing your experiences - this is exactly the kind of real-world guidance you can't get from reading IRS publications alone!

This is exactly the kind of situation that drives taxpayers crazy! I went through something similar two years ago and learned the hard way that converted properties create a unique reporting requirement. The key point everyone here is making is absolutely correct - you need BOTH forms because you're dealing with two different tax treatments for the same property sale: 1. Form 8949 for the capital gain portion (which gets excluded under Section 121) 2. Form 4797 for the depreciation recapture portion (which is still taxable regardless of the exclusion) The $12,000 in depreciation you mentioned is crucial - that amount will be taxed at up to 25% even though your capital gain is excluded. TurboTax's approach of only using Form 8949 is missing this critical piece. I ended up having to manually override TurboTax by entering the sale as "business property" to force Form 4797, then adjusting the capital gain portion to reflect the Section 121 exclusion. It's not intuitive, but it's necessary to report everything correctly. If you're not comfortable doing this manually, I'd strongly recommend either using the AI analysis tools mentioned here or getting a consultation with a tax pro. The IRS is very particular about depreciation recapture reporting, and missing it could definitely trigger unwanted attention later.

Can I just say how annoying it is that all this tax stuff isn't taught in school?? I have a master's degree but still had to google "what is an EIN" when I started freelancing. The IRS instructions might as well be written in another language lol

Great question! As others have mentioned, you don't technically need an EIN as a sole proprietor, but I'd definitely recommend getting one for the privacy protection alone. I've been freelancing for about 3 years now and got my EIN right from the start. One thing I'd add is that having an EIN can also make it easier to separate your business finances from personal ones. Even though you're not required to have a separate business bank account as a sole proprietor, many banks prefer an EIN when opening business accounts. This makes tracking your business income and expenses much cleaner come tax time. The application process through the IRS website is straightforward and takes maybe 10-15 minutes. Just make sure you apply directly through the official IRS site (irs.gov) - there are a lot of third-party sites that will charge you fees for something that's completely free from the IRS. Also, since you're making steady income ($1200/month is great!), don't forget about quarterly estimated tax payments. You'll likely owe both income tax and self-employment tax on that freelance income.

I've been in HR for over 15 years and have dealt with countless FSA situations like this. What you're describing is unfortunately very common, but the good news is that you have several strong factors working in your favor. First, the fact that you were a 5-year employee and your husband still works there gives you significant leverage. Most employers want to maintain good relationships with current employee families, and they understand that these situations can genuinely happen due to miscommunication. Second, the timing of your expenses is crucial - if your daycare costs were incurred while you were actively employed (before April), you have a legitimate case for an exception. This isn't about bending rules; it's about recognizing that the actual benefit usage occurred during your employment period. Here's what I'd recommend for your HR meeting: 1. Request the complete Summary Plan Description (SPD) - not just the basic plan overview. Look for any language about "plan administrator discretion" or "reasonable accommodations." 2. Document exactly what communication (if any) you received about FSA deadline changes upon termination. If this wasn't clearly communicated, it strengthens your case significantly. 3. Emphasize that your family acted in good faith by staying within annual limits and having your husband open his own FSA after you left. Most plan documents do include some discretionary language for situations exactly like yours. The key is approaching this as a plan administration review rather than just asking for a favor. Your long employment history and current family employee status make you an ideal candidate for an exception. Don't give up after one conversation if the initial response isn't positive. These decisions can often be escalated to a benefits committee or senior leadership level.

This whole thread has been incredibly educational - I had no idea there were so many potential options for FSA situations like this! As someone who's terrified of making similar mistakes with my own benefits, I wanted to ask: are there any proactive steps we should all be taking to avoid these kinds of deadline mix-ups when changing jobs? It seems like the communication around FSA deadline changes during termination is pretty hit-or-miss across different employers. Should we be specifically asking about this during exit interviews, or requesting certain documents before we leave? Also, for those of you who have successfully recovered FSA funds through these various methods (employer exceptions, Summary Plan Description reviews, etc.), how long did the whole process typically take from start to finish? I'm wondering if there are time-sensitive aspects to these appeals that people should be aware of. Really hoping OP's HR meeting goes well! This community has provided such valuable insights that I'm bookmarking this whole thread for future reference.

Don't forget about the impact of realizing $1.3 million in gains on your Medicare premiums two years from now! With income that high, you'll likely hit the top IRMAA bracket for Medicare Part B and D premiums. In 2025, your premiums would be based on your 2023 income. For single filers with income above $500,000, the monthly Part B premium jumps to around $500-600 per month (vs the standard $170ish). Just something else to budget for since this kind of one-time capital gain has lingering effects on your retirement expenses.

This is a great discussion! As someone who went through a similar situation a few years ago, I wanted to add that it's also worth considering the timing of when you realize these gains if you have any control over it. If you're planning to have lower income in future years (which is common in retirement), you might benefit from spreading the gains across multiple tax years to stay in lower capital gains brackets. The 0% bracket goes up to about $44k, and the 15% bracket extends to around $492k for single filers. Also, if you're doing any charitable giving, this could be a great year to consider donating appreciated securities directly to charity rather than cash. You avoid the capital gains tax entirely and still get the charitable deduction. With $1.3M in gains, even a modest charitable giving strategy could save significant tax dollars. Just another angle to consider while you're planning!

Has anyone noticed that tax software seems to get confused with inherited IRAs? I've used three different programs over the years and they ALL struggle with this scenario. I wish they would update their interfaces to make these questions clearer for situations like this!

I went through this exact same situation two years ago when my grandmother passed away and left me part of her IRA. The tax software confusion is real - I think the issue is that these programs are designed primarily for regular IRA distributions, not inherited ones. One thing that helped me was understanding that the "basis" question is really asking whether the original owner ever made contributions with money that was already taxed (after-tax contributions). Most traditional IRAs are funded entirely with pre-tax dollars, so there's usually no basis to worry about. The key is to look at your 1099-R form carefully. If Box 2a (taxable amount) equals Box 1 (gross distribution), then there's no basis and the entire amount is taxable. If Box 2a is less than Box 1, that might indicate some after-tax contributions were made. Since you confirmed with the financial institution that there were no after-tax contributions, you should be fine selecting "inherited IRA = Yes" and "basis = No" and then manually correcting any weird refund calculations the software produces. The important thing is that you report it as an inherited distribution so it's properly coded on your return.