I filed an estate tax return using Turbo Tax last year and regretted it. The software doesn't explain the complex interplay between estate administration expenses and income distribution deductions. I ended up having to amend the return after learning I could have saved about $3,200 in taxes by making different elections.

Based on what you've described with your uncle's estate - the house, investments, and business sale - I'd strongly recommend going with a CPA for at least this first filing. Estate tax returns involve some tricky concepts that even experienced individual tax filers can struggle with. The business sale proceeds alone could involve depreciation recapture, capital gains calculations, and potentially installment sale treatment depending on how it was structured. With three beneficiaries, you'll also need to navigate income distribution deductions and make strategic decisions about when and how much to distribute to minimize the overall tax burden. I made the mistake of trying to handle my father's estate return myself using tax software and ended up costing the estate thousands in missed deductions and suboptimal elections. A good CPA who specializes in estates will often save more than their fee through proper tax planning. You can always learn from working with them this year and potentially handle simpler future filings yourself once you understand the process better. As executor, your fiduciary duty is to maximize the estate's value for beneficiaries - sometimes that means spending money on professional help upfront.

This thread has been incredibly helpful! I'm dealing with the exact same situation - got a 1099-DIV with capital gain distributions in box 2A even though I never sold anything. It's reassuring to know this is totally normal and that I'm not missing something obvious. One thing I wanted to add for anyone else reading this: make sure you keep good records of these distributions, especially if you're reinvesting them automatically. Your brokerage should track your cost basis automatically now (they're required to), but it's still smart to keep your own records. When you do eventually sell years down the road, you'll want to make sure you're getting credit for all the taxes you paid along the way through these distributions. Also, if you have these investments in a tax-advantaged account like a 401(k) or IRA, you don't have to worry about any of this - the distributions happen inside the account without creating a current tax bill.

This is exactly the kind of confusion that trips up so many people! You're definitely not alone in being surprised by capital gains on your 1099-DIV when you didn't sell anything personally. What's happening is that your mutual fund or ETF had to sell some of its underlying holdings during the year (maybe to rebalance, meet redemptions, or because the fund manager changed strategy), and those sales generated capital gains. By law, the fund has to distribute almost all of these gains to shareholders like you by year-end to avoid paying corporate taxes. So yes, you do need to report and pay taxes on box 2A (capital gain distributions), plus boxes 1a and 1b if they have amounts. The good news is that these capital gain distributions are usually taxed at the more favorable long-term capital gains rates rather than ordinary income rates. One tip: if this kind of surprise tax bill bothers you, consider looking into more tax-efficient funds (like broad market index funds) for your taxable accounts in the future. They tend to generate fewer unexpected distributions because they trade less frequently inside the fund.

Has anyone used those donation receipt tracking apps? I tried ItsDeductible last year and it was ok but not great for higher value items.

Your 18% donation rate is actually quite reasonable and shouldn't be a red flag by itself. I've seen clients donate 25-30% of windfalls without issues, especially when it's a one-time event like a property sale. The most important thing is having proper documentation for each donation. Since you mentioned keeping all receipts, make sure you have written acknowledgments from each charity for donations of $250 or more. These need to include the donation amount, date, and a statement that no goods or services were provided in exchange (or describe what was provided). One tip for future years: if you're planning to continue higher donation levels, consider establishing a pattern by documenting your charitable giving philosophy or creating a simple giving plan. This shows intentionality rather than randomness, which auditors prefer to see. The fact that TurboTax isn't flagging anything is also a good sign - their built-in audit risk assessment is pretty conservative. Your documentation sounds solid, so I wouldn't stress too much about it.

I'm dealing with a similar situation right now and wanted to share what my tax preparer told me. Since you haven't lived in the house for 5+ years, you won't qualify for the primary residence exclusion, but don't panic about the documentation issue. The IRS has specific guidelines for "adequate records" and they recognize that homeowners don't always keep perfect documentation. Here's what my CPA suggested as a systematic approach: **Start with what you definitely have:** - Any financing records (mortgages, home equity loans, credit lines used for improvements) - Photos with timestamps from your phone or social media - Any permits you can find through your city/county records **Then reconstruct methodically:** - Create a timeline of all improvements by year - Search all email accounts for contractor communications - Check bank/credit statements for large purchases at home improvement stores - Look for any insurance claims or policy updates related to the improvements **For valuation:** - Use cost estimation tools like RSMeans or local contractor websites to establish reasonable market rates for the work done in those specific years - Your sister might have better records since she stayed in the house - definitely coordinate with her The key is showing good faith effort to reconstruct accurate records. The IRS allows reasonable estimates when original documentation is lost, as long as you can support your numbers with some form of evidence. Don't let the fear of imperfect records stop you from claiming legitimate improvements that significantly increase your basis.

As someone who went through a similar situation with capital gains and missing receipts, I want to emphasize that you're not stuck with a massive tax bill! The key is being thorough and systematic in reconstructing your records. Here's my recommended action plan based on what worked for me: **Immediate steps:** - Contact your sister ASAP to coordinate - she may have kept records you forgot about since she handled the house after you moved - Pull all bank and credit card statements from 2013-2018 and highlight every home improvement expense - Search ALL your email accounts using keywords like "contractor," "renovation," "quote," "invoice," "Home Depot," etc. **Documentation goldmines people often overlook:** - Your county's permit database (usually searchable online by address) - Property tax assessment records showing value increases after improvements - Homeowner's insurance policy updates reflecting increased coverage - Social media posts with dated photos of renovation progress - Text message archives if you backed up your phone **For the major projects you mentioned:** - Kitchen renovation (2016): Check for any home improvement loans, appliance purchase records, or contractor communications - Roof replacement: This almost certainly required a permit - check county records - Windows: Energy efficiency rebates from utility companies sometimes have records - Bathroom renovations: Plumbing permits are common for full bathroom remodels The IRS accepts "reasonable reconstruction" when original records are unavailable. Create a detailed spreadsheet with your best estimates supported by whatever evidence you can gather. Even if you can only document 70-80% of your actual improvements, that could still save you thousands in capital gains taxes. Don't give up - you have more documentation than you think!

One thing I'm not seeing mentioned is the timing. Getting married in December 2025 vs January 2026 makes a HUGE difference for taxes. The IRS considers you married for the ENTIRE tax year even if you get married on December 31st. So if they just got married, they'll be "married filing jointly" for the entire 2025 tax year when they file in 2026.

As a tax professional, I want to address a few key points here. First, the $10k difference you calculated seems unusually high for those income levels - typically the marriage bonus for a $145k/$32k couple would be in the $3-5k range as others have mentioned. You might want to double-check those TurboTax calculations. That said, your friend will likely see some legitimate tax benefits. With such disparate incomes, married filing jointly usually results in savings because the higher earner's income gets "averaged" with the lower earner's income, potentially moving more income into lower tax brackets. However, I echo what others have said - marriage is a huge legal and financial commitment that goes far beyond taxes. It affects debt liability, property rights, inheritance, healthcare decisions, and more. If they were already planning to marry eventually, then this might have just accelerated their timeline. But if taxes were the primary driver, that's concerning. My advice: sit down with your friend, acknowledge that you may have been overzealous about the tax benefits, and suggest they speak with a tax professional to get accurate numbers. Most importantly, be supportive of their marriage regardless of how it started - they're the ones who ultimately made the decision.