This thread has been incredibly helpful! I'm dealing with a PFL situation myself and had no idea about some of these nuances. One question I haven't seen addressed - what happens if you received PFL benefits in December but didn't actually take the leave until January of the following tax year? My daughter was born in late December, but I didn't start my actual leave until after the New Year due to how my company handles their leave policies. I received a lump sum payment in December for the upcoming leave period. Should this be reported on my 2024 return even though the leave itself was in 2025? I'm worried about getting this timing wrong since it seems like there are so many ways to mess up PFL reporting. Also, has anyone dealt with PFL from multiple states? We moved mid-year and I'm not sure if I need to file anything special since I was paying into one state's program for part of the year but used a different state's program for the actual leave.

I went through this exact same confusion with TurboTax and PFL benefits! You're right to be careful about getting it correct - the reporting requirements can be tricky. First, check your mail and online portals for a 1099-G form from your state's family leave program. This form should show the total PFL benefits you received and any taxes that were withheld. The 1099-G is separate from your W-2 because the payments come from the state fund, not directly from your employer. When you enter the 1099-G information in TurboTax, make sure you're putting it in the "Government Payments" or "1099-G" section, not trying to add it to your W-2 wages. TurboTax will walk you through this when you get to that section. One important thing to double-check: if your employer provided any "top-up" payments to supplement the state benefits (bringing you closer to your full salary), those employer contributions WOULD appear on your W-2. But the base PFL payments from the state should only be on the 1099-G. If you haven't received your 1099-G yet, contact your state's PFL department - they usually have online portals where you can access or request these documents. Don't file without it, as you'll likely need to amend your return later if you miss reporting this income.

I inherited a nonqualified annuity last year too, and my situation was slightly different. My tax preparer said I absolutely needed the 1099-R to properly file, even though taxes were withheld. Has anyone used H&R Block or TurboTax for this kind of situation? I'm trying to figure out which would handle this better.

I'm dealing with a very similar situation with my grandmother's nonqualified annuity that I inherited last year. The missing 1099-R is definitely a red flag - I received mine from the insurance company even though they withheld the correct amount of taxes. Here's what I learned from my tax preparer: even if the annuity company calculated and withheld taxes correctly, you still need to report the distribution on your tax return. The 1099-R shows the IRS that you properly accounted for the income and any withholding. I'd strongly recommend calling Nationwide again and asking specifically for the tax reporting department. When I had issues getting my 1099-R, I had to escalate beyond the general customer service reps. They should be able to reissue it or at least explain in writing why one wasn't generated. Don't spend that money you set aside until you get this resolved - better safe than sorry when it comes to the IRS. The fact that taxes were withheld is good, but without proper documentation, you could run into issues during filing or if audited later.

I see everyone giving great advice about the tax filing status, but something else to consider - make sure you're tracking ALL the medical expenses. When my wife became disabled, we missed out on thousands in deductions the first year because we didn't realize what all qualified. Don't just include the obvious doctor visits and prescriptions. Track mileage to medical appointments, home modifications, specialized equipment, even air purifiers if prescribed by a doctor. We installed a ramp and widened doorways which partially qualified as medical expenses!

One more thing that might help - if your wife qualifies for SSDI eventually, there's something called the "trial work period" that could affect your taxes. During this period (up to 9 months), she can attempt to work while still receiving disability benefits. Any income during this time would need to be reported on your joint return. Also, don't forget about the Earned Income Tax Credit (EITC) if your household income falls within the qualifying range. Many people overlook this credit, but with only one working spouse and medical expenses, you might qualify for a significant refund. The income limits are higher for married filing jointly, and having a disabled spouse doesn't disqualify you. I'd strongly recommend keeping a detailed spreadsheet of ALL medical-related expenses throughout the year - parking fees at hospitals, over-the-counter medications (if prescribed), medical alert systems, even special foods if medically necessary. These small expenses add up quickly and can push you over that 7.5% AGI threshold for itemizing.

Great question about international property sales! I went through something similar when I sold inherited property in Canada. A few additional points that might help: Make sure you understand the timing of when you'll owe taxes. Even though you'll receive the money this year, you won't actually pay the capital gains tax until you file your return next year (unless you need to make estimated quarterly payments). If this creates a large tax liability, you might want to set aside 20-25% of the proceeds immediately so you're not scrambling next tax season. Also, consider the impact on your overall tax situation. A large capital gain in one year might push you into a higher tax bracket for other income, or it could affect eligibility for certain tax credits or deductions. Sometimes it's worth consulting with a tax professional to see if there are any strategies to minimize the overall impact. One last thing - keep detailed records of all costs associated with the sale (legal fees, transfer taxes, real estate agent commissions, etc.) as these can typically be deducted from your capital gain, reducing your tax liability. These costs can add up to several thousand dollars and make a meaningful difference in what you owe.

This is such a comprehensive discussion! I wanted to add one more consideration that might be relevant - the potential impact on your Net Investment Income Tax (NIIT) that was briefly mentioned earlier. Since you're looking at $120k-180k in proceeds, and depending on your other income, you might trigger the 3.8% NIIT on top of your regular capital gains tax. This kicks in when your modified adjusted gross income exceeds $200k for single filers or $250k for married filing jointly. Also, something I learned the hard way - make sure to notify your bank in advance about the incoming large international wire transfer. Even though it's legitimate, I've seen cases where banks temporarily freeze accounts when large unexpected international transfers arrive, especially if it's not typical activity for your account. A simple call to your bank's wire department beforehand explaining the expected transfer can save you potential headaches. Lastly, consider opening a separate savings account specifically for setting aside the tax money as soon as the funds arrive. With current interest rates, you can at least earn something on the money you'll eventually owe to the IRS rather than letting it sit in checking. Just make sure it's easily accessible for when you need to pay quarterly estimated taxes or your final tax bill. You're being very smart to plan this out in advance - most people don't think about these implications until after they've already received the money!

As someone who just went through their first job change in several years, I can't emphasize enough how valuable this Box 12 DD information has been for making informed decisions! When I was comparing offers, I created a simple spreadsheet that included base salary plus the estimated Box 12 DD value (I asked HR departments for their typical contribution amounts). The difference was eye-opening - what looked like a $3,000 salary cut actually turned out to be a $5,000 total compensation increase when I factored in the better health benefits. One practical tip: if you're interviewing and the company can't provide specific Box 12 DD estimates, ask them what percentage of health premiums they typically cover. Most companies cover 80-90% for employee-only coverage, and you can use that to estimate the value. For a family plan that costs $20,000 annually, an 85% employer contribution means about $17,000 in Box 12 DD value. I also started using this information to better appreciate my current benefits during annual reviews. Instead of just focusing on salary increases, I now look at total compensation changes. Last year my salary went up 3%, but healthcare costs rose significantly and my employer absorbed most of that increase - so my real compensation grew by more like 6%. This thread really should be bookmarked by anyone trying to understand their W-2 or evaluate job offers. The practical insights here are gold!

This thread has been absolutely fantastic for understanding Box 12 DD! As someone who's been staring at this code on my W-2 for years without really knowing what it meant, I'm amazed by how much practical wisdom has been shared here. What really struck me is how this one little box connects to so many bigger financial decisions - job comparisons, career transitions, FSA planning, and even just appreciating what you currently have. I never realized that my employer's $9,800 contribution (shown in my Box 12 DD) was essentially like getting an extra month's salary that I wasn't even accounting for. The job search strategies shared here are game-changing. I'm definitely going to start asking for Box 12 DD estimates during interviews and creating that total compensation spreadsheet that @Makayla Shoemaker mentioned. It's wild to think how many job decisions people make without considering this significant component of their package. One thing I'm curious about - for those who've been tracking these amounts over time, have you noticed any correlation between company financial performance and how they handle healthcare cost increases? It seems like this could be an early indicator of how stable your employer's benefits program is. Thanks to everyone who shared their experiences and resources. This is exactly the kind of practical financial education that makes a real difference in people's lives!