This is really helpful! How did you calculate the value of housing and food to determine that you provided more than half her support? I'm trying to figure out how to quantify that properly.

For housing, I used the fair rental value of the room she stayed in (looked at comparable rooms for rent in our area) plus a percentage of utilities based on our household size. For food, I tracked grocery expenses for a couple months and calculated her portion based on that. I also included car insurance since we added her to our policy, cell phone costs since she was on our family plan, and medical expenses we covered. For her part of the support equation, I included her earnings from her part-time job, scholarships that covered room and board (not tuition), and any other financial help she received. The IRS has a worksheet in Publication 501 that helps with this calculation. The key is being able to show that your contribution exceeded 50% of her total support from all sources. In our case, the housing value alone was significant enough to clearly demonstrate we provided most of her support.

On TurboTax you should select "Other" when it asks for the relationship. Then when it asks if this person lived with you all year, select "Yes" (assuming they did, or if they were away at college but your home was their main residence). There's also a section where it will ask you to verify that you provided more than half their support.

That's an interesting approach I hadn't considered! About how much do you typically underwithhold? And do you just make equal quarterly payments, or is there some calculation involved? I'm intrigued by the idea of having more control over our money throughout the year.

We typically underwithhold by about 15% of our total expected tax liability. For someone in your situation, that might mean underwithholding by around $30,000 total for the year, or $2,500 monthly that stays in your accounts instead of going to the IRS. The quarterly payments don't have to be equal if your income fluctuates, but we keep it simple and just divide our expected shortfall by 4. The payment due dates are April 15, June 15, September 15, and January 15 of the following year. You can make them online at the IRS website using Direct Pay or EFTPS. Just make sure you're meeting that safe harbor of 110% of your previous year's tax liability (since you're over the $150k AGI threshold). That's the easiest way to guarantee no penalties regardless of this year's actual liability.

I use it all the time and find it really accurate, but it's crucial that you include ALL income sources, not just your W-2 jobs. Make sure you're entering things like investment income, rental properties, etc. The other key is to update it quarterly since your situation might change throughout the year.

I think I've already missed that window since it's been about 11 months since her passing, and as you mentioned, I've already completed the rollover into my 401K. I feel like I should have researched this better before making the initial decision, but I was dealing with a lot emotionally and just followed what the HR person at her company suggested.

That's understandable - these decisions often need to be made during difficult emotional times. Since the disclaimer option is no longer available, your best approach now is probably a combination strategy: First, designate her brother as the beneficiary for that portion of your 401K, ensuring he'll receive it if something happens to you. Then, work out a yearly gifting strategy once you're eligible for qualified distributions without penalties. You might also consult with an attorney about creating a simple agreement documenting your intentions, which could help clarify things for your own estate planning. Don't be too hard on yourself - you're trying to do the right thing in a system that doesn't make it easy.

This is actually not great advice. 401K loans become immediately due if you leave your job, and since OP is living overseas, that could be risky. Plus, if you can't repay the loan, it becomes a distribution with all the taxes and penalties. The gift tax concerns would still apply too.

Does Wave let you export reports that work for tax filing? That's been my biggest pain point.

Yes, you can export expense reports as PDFs or spreadsheets that work well for tax filing. The reports show all the transaction details and categories that match up with Schedule C. You can also generate specific date range reports, like quarterly or annual. The only limitation I've found is that the automatic categorization isn't always perfect, so I do have to go in and correct some entries occasionally. But for a free tool, it's pretty solid and has saved me tons of time compared to my old method of manually tracking everything in spreadsheets.

Oof that's rough. What app are you using now that has the cloud sync? I travel a lot for work and my biggest fear is losing all my trip receipts.

Do you remember what the monthly payment amount was for your $5,800 balance? I'm trying to figure out if they let you choose how much to pay each month or if they assign an amount.

You generally can choose your monthly payment amount as long as the debt will be paid off within the required timeframe. For amounts under $10,000, that timeframe is 3 years (36 months). So in my case, the minimum payment would have been about $161 per month not including interest and penalties. I actually opted to pay $200 per month to account for the ongoing interest and penalties and to clear the debt faster. They let me choose this amount during the application process. I set up direct debit from my checking account to avoid having to remember to make the payments and to get the lowest setup fee.

Completely agree about filing on time! The failure-to-file penalty is 5% of the unpaid taxes for each month your return is late, up to 25%. The failure-to-pay penalty is much lower at 0.5% per month.

Thank you for pointing this out! He did file on time, he just couldn't pay the full amount at once. I'll definitely suggest he try the online system since that seems to be the consensus here - much easier than trying to call again.