As someone who's helped dozens of coworkers through relocation packages, I want to emphasize something that often gets overlooked: timing matters a lot for your overall tax situation. If your company processes the relocation payment late in the year, you might not have enough remaining paychecks to properly spread out the tax impact through normal withholding. I've seen cases where someone got their relocation gross up in November, and even though the calculation was technically correct, they ended up owing money at tax time because the withholding system couldn't account for their full year tax bracket properly with only a few paychecks left. If you're planning a move, try to time the relocation payment earlier in the year if possible. This gives the payroll system more pay periods to accurately calculate your withholding and helps avoid any surprises. Also, keep all your relocation documentation - receipts, the gross up calculation from HR, everything. You'll want it for your tax preparer and for your own peace of mind when reviewing your W-2. One last tip: if your company offers it, consider asking for a "tax equalization" calculation instead of just gross up. This accounts for the broader tax impacts that others have mentioned here, not just the direct taxes on the relocation benefit itself.

I've been through this exact situation and want to add something that really helped me understand it better. Think of gross up withholding like this: your employer is essentially "buying" you the tax liability that comes with their relocation benefit. When they give you $27k for relocation, that becomes taxable income to you. But since you didn't ask for taxable income - you just needed help moving - they calculate how much extra money they need to give you to cover ALL the taxes on the entire amount (including the extra amount itself). It's like a recursive calculation. Here's what I wish someone had told me: the gross up amount often looks scary on your paystub because it can nearly double the relocation benefit amount. In my case, a $20k relocation became about $35k total income on my W-2 due to the gross up. But that extra $15k wasn't "free money" - it was specifically calculated to pay the taxes on the full $35k. One practical tip: if you're planning to use a tax preparation service, give them a heads up about the relocation gross up when you make your appointment. It's not complicated for them to handle, but it helps if they know to expect it so they can explain exactly how it affected your return.

Just wanted to add my experience from last year - I inherited my father's house and initially thought I could skip the appraisal since I wasn't planning to sell. Big mistake! When I finally decided to sell 18 months later, I had to scramble to get a retrospective appraisal done. The appraiser I found was great (found her through the Appraisal Institute like Emma suggested), but she explained that the further you get from the date of death, the harder it becomes to find truly comparable sales from that exact time period. Market conditions change, and what might seem like a similar property sale from 6 months later could have very different market factors affecting it. My advice: even if you're 100% sure you'll never sell, get the appraisal done within the first few months. The cost is minimal compared to the potential headaches and tax issues down the road. Plus, life circumstances change - you might need to sell for reasons you can't predict right now.

I've been following this thread and wanted to share something that might help others avoid the stress I went through. When my grandfather passed last year, I was in a similar boat - inherited his duplex property and wasn't sure about the appraisal timing. What really helped me was getting connected with an estate planning attorney who specialized in inherited property. They explained that beyond just the step-up basis issue, there are also state-specific rules that can affect your tax situation. In my state, for example, there were additional inheritance tax considerations that I would have completely missed if I'd just focused on the federal requirements. The attorney had a network of appraisers they regularly worked with who were experienced in estate valuations, which saved me the headache of trying to find someone qualified on my own. The whole process ended up being much smoother than I expected, and having professional guidance gave me confidence that I was handling everything correctly. For anyone feeling overwhelmed by this stuff - don't try to navigate it all alone. Sometimes spending a few hundred on professional advice upfront can save you thousands in mistakes later.

Theres another angle to consider - if ur trading in both taxable and IRA accounts and do these transactions across accounts, the wash sale rules still apply but ur broker might not track them correctly. Made this mistake last yr and got hit with an unexpected tax bill 😩

Great question about cross-account wash sales! You're absolutely right that brokers often miss these. The IRS considers SPY and VOO to be substantially different securities even though they track similar indexes. SPY tracks the S&P 500 while VOO is Vanguard's S&P 500 ETF - they're different enough that selling SPY options at a loss and buying VOO shares wouldn't trigger the wash sale rule. However, if you sold SPY options and bought SPY shares (or other SPY options) across accounts, that would definitely be a wash sale that you'd need to track manually since your broker won't catch it.

Just went through this exact situation with my father's life insurance policy earlier this year. The $78,000 payout you received is not taxable income, which is why you didn't get a 1099 - insurance companies aren't required to send them for death benefits. However, I'd recommend double-checking your payout statement to see if any portion was labeled as "interest." In my case, there was about $2,400 in interest that accumulated between my dad's death date and when they finally cut the check (took them 6 weeks to process). That interest portion IS taxable and should have generated a 1099-INT form. If you find interest on your statement but didn't receive a 1099-INT, you'll still need to report it as income even without the form. The insurance company might have just been slow sending it out - mine didn't arrive until late February.

I went through something very similar when my grandfather passed last year. The key thing that helped me was requesting a detailed breakdown from the insurance company showing exactly what comprised the total payout. Most companies will provide this if you ask specifically for it. In my case, the $85,000 total included $82,100 in actual death benefits (completely tax-free) and $2,900 in interest that accrued during their processing delay. Only that interest portion required tax reporting. One thing to watch out for - some insurance companies will lump everything together on the initial payout statement, so you really need to ask for the itemized breakdown. Also, if your aunt had any outstanding policy loans against the life insurance, that can sometimes complicate the tax situation, though it doesn't sound like that's your case. Since you mentioned the insurance company gave you the runaround, I'd suggest asking to speak specifically with their "tax documents" or "1099 department" when you call back. They're usually more knowledgeable about these reporting requirements than general customer service.

I'm going through the exact same thing! I've been using Free File Fillable Forms for about 4 years now and this new interface has me completely stumped. What used to be a simple, straightforward process now feels like I'm learning an entirely new system from scratch. The most frustrating part for me is that I actually started my return last weekend, got about halfway through, and when I came back to finish it this week, I couldn't figure out how to get back to where I left off. The new navigation is so different that I'm not even sure if my work was saved properly. I really appreciate everyone sharing their tips about finding the "Start New Tax Return" button and the manual save requirements. It's ridiculous that we have to crowdsource basic navigation instructions, but at least we're all helping each other out. The free filing is still worth it compared to paying for tax software, but they really dropped the ball on the user experience this year. Has anyone found a way to view or recover partially completed returns in this new system? I'm worried I might have to start over completely, which would be incredibly frustrating after spending hours on it already.

I'm experiencing the exact same frustration! Been using Free File Fillable Forms for the past 3 years and this new interface completely threw me for a loop. What used to take me maybe 2-3 hours to complete now feels like it's going to take all weekend just because I can't figure out where anything is. The thing that really bugs me is that they clearly spent a lot of time and money redesigning this system, but it feels like they forgot about the people who actually use it regularly. The old interface wasn't fancy, but it was predictable and efficient. Now I'm spending more time trying to navigate the interface than actually filling out my tax forms. I'm definitely going to try some of the suggestions mentioned here, especially that taxr.ai tool that helps with navigation. At this point I'm willing to try anything that can help me get through this without pulling my hair out. Thanks everyone for sharing your experiences - it's reassuring to know I'm not the only one struggling with this "upgrade"!