That's a really good point about currency risk that I hadn't considered! Do you know if there are any tax-efficient ways to manage currency conversion when sending money back to the US? I'll still have some student loans and a car payment in USD.

There aren't specific tax advantages for currency conversion, but you might want to look into services like Wise (formerly TransferWise) or OFX for better exchange rates than banks offer. The conversions themselves aren't tax events unless you're actually trading currencies as investments. For your US debts, you might consider keeping a US bank account open and periodically transferring larger sums to minimize conversion fees, rather than monthly smaller transfers. Some expats also maintain US credit cards for US-based recurring payments while living abroad, which can simplify things.

This is so important and often overlooked! I worked in Canada for 7 years and then moved back to the US. When I applied for Social Security benefits, they initially calculated without my Canadian work history. I had to specifically request they consider the totalization agreement, which increased my monthly benefit by about $300!

The Donor Advised Fund sounds interesting! If I bunch several years of donations together, would that help me stay under the IRMAA threshold for multiple years, or just give me one good year and then potentially push me over in subsequent years? Also, do you know if medical premiums count toward that 7.5% threshold? I have some pretty hefty supplemental insurance costs.

Bunching donations can give you one year with a lower MAGI, which helps with IRMAA for just that determining year. You're right that you'd need to plan for the subsequent years too - that's where QCDs become helpful since they can reduce your taxable income each year without needing to itemize. Yes, your premiums for Medicare Part B, Part D, Medicare Advantage, and supplemental policies all count toward the 7.5% medical expense threshold! Many retirees don't realize this. Track all your out-of-pocket medical costs including dental, vision, hearing aids, and long-term care insurance premiums too. With the higher healthcare costs in retirement, you might be surprised how often you can clear that 7.5% threshold.

That's really interesting! How much did you have to invest to make it worthwhile from a tax perspective? I've been thinking about helping my son with his landscaping business but wasn't sure if it would make a meaningful impact on my taxes.

Pro tip: if you want less tax withheld from your bonus, increase your 401k contribution just for that paycheck if your company allows it. I put 50% of my bonus straight into 401k last year and it lowered my taxable income. Double win!

This is actually a really important point! My bonus pushed me into a higher tax bracket last year because it came in December. If it had come in January, my tax situation would have been completely different. Timing matters!

Would moonlighting at an urgent care for even just a few shifts count for this? I'm in a similar situation (different professional liability insurance though) and wondering if even just a few thousand in 1099 income would help establish the business intent.

Yes, moonlighting at an urgent care as a 1099 contractor would absolutely help establish business intent. Even just a few shifts generating a couple thousand dollars would create a much stronger case that you were genuinely engaged in business activity related to the insurance expense. The key is making sure you're actually classified as an independent contractor (receiving a 1099) rather than a part-time employee (W-2). As long as you have some legitimate 1099 income from medical work, you'll be in a much better position to justify the large deduction on Schedule C.

Thank you so much for this insight! I hadn't even considered the self-employment tax angle. The more I think about it, the more I'm leaning toward filing Schedule C with the full expense. I actually do have some very minimal income (around $3K) from chart reviews I did while transitioning between jobs. That should help establish business intent, right? I'm thinking I'll use some combination of the advice here - documenting everything thoroughly, including my correspondence with the locums company about credentialing, and making sure I'm prepared in case of an audit. The tax savings between Schedule C vs. effectively no deduction on Schedule A is just too significant to ignore.

What exactly is the carried interest loophole? I hear about it but don't really understand how it works or why it's such a big deal.

Carried interest is basically the share of profits that hedge fund and private equity managers get as compensation for managing investments. Instead of being taxed as ordinary income (which can be up to 37%), it's taxed at the capital gains rate (usually 20%). So imagine a fund manager who makes $10 million from managing other people's money. Instead of paying $3.7 million in taxes like other high-earning professionals would, they might only pay $2 million. That's a $1.7 million tax break just because of how their compensation is classified! Meanwhile teachers, doctors, and engineers all pay the higher ordinary income rates on their earnings.

That would totally screw over people in high cost of living areas though. $500k won't even buy you a 1 bedroom condo in San Francisco or NYC. Not everyone with a mortgage over $500k is wealthy - many are middle class families in expensive metro areas.