One thing to be careful about is keeping very detailed records of the support calculation. The IRS may scrutinize foreign dependent claims more closely, so you'll want to document not just the medical expenses but ALL support you provide versus what your parents pay for themselves. Create a spreadsheet tracking monthly expenses: housing costs, utilities, food, medical care, transportation, etc. Include both what you send and what your sister handles on your behalf. This will help prove you're providing over 50% of their total support. Also, consider having your parents sign a statement (in both Thai and English) acknowledging that you provide their primary financial support. While not required, this can be helpful documentation if the IRS has questions about your dependent claims. The ITIN application process can take several months, so start that early. You'll need certified copies of their passports and possibly other identity documents from Thai authorities.

One additional consideration for your situation - since you're dealing with foreign medical expenses, make sure to convert all Thai baht amounts to USD using the exchange rates from the dates when the expenses were actually incurred, not just a single year-end rate. The IRS requires you to use the exchange rate from the transaction date for each expense. I'd recommend keeping a log of exchange rates alongside your expense records. You can use the IRS's yearly average exchange rates as published in their Revenue Procedures, or daily rates from sources like xe.com or the Federal Reserve. This becomes especially important if the Thai baht fluctuates significantly during the year. Also, be aware that if you're sending money through services like Western Union or bank wire transfers, those transaction fees are generally NOT deductible as medical expenses, even though they're necessary to get the money to your parents for their care. Only the actual medical and caregiving costs qualify. The good news is that caregiver expenses for your parents can be substantial and are generally deductible as long as the care includes some medical component (not just companionship). Make sure to get documentation showing the caregiver helps with medical needs like medication management, mobility assistance, or other health-related activities.

Wait... are you SURE you know all your profits/losses exactly? Did u account for wash sales????? That's where most ppl mess up with self-calculating. Robinhood doesnt make it obvious in the app when wash sales happen but they report them on the 1099!!!

I'm going through this exact same situation right now! Reading through all these comments has been super helpful. I think I'm convinced to just wait for the official 1099 from Robinhood rather than risk the headache later. @Angel Campbell - your story about the amended return really sealed the deal for me. The stress and extra costs just aren't worth trying to save a few weeks. Plus after seeing the discussion about wash sales, I'm realizing there might be things I missed in my own calculations that could cause problems. Does anyone know if there's a way to check when Robinhood typically sends out their forms? I know the legal deadline is February 15th, but wondering if they usually get them out earlier than that.

Has anyone had experience with hybrid policies? My financial advisor keeps pushing this combo life insurance/LTC policy that supposedly has tax advantages, but I'm having trouble finding clear info on how to report the premiums.

Great question about LTC premiums! Just to add to what others have shared - make sure you keep detailed records of your premium payments throughout the year. The IRS may want to see documentation that your policy is indeed qualified LTC insurance if you're audited. Also, don't forget that if either of you becomes self-employed in the future (even part-time consulting), the rules change significantly in your favor. Self-employed individuals can deduct LTC premiums as an above-the-line deduction (on Schedule 1) up to the age-based limits, which means you don't have to meet the 7.5% AGI threshold or itemize to get the benefit. One more tip: if you're planning any major medical expenses this year (dental work, surgery, etc.), it might push you over that 7.5% threshold where your LTC premiums would actually provide a tax benefit. Worth running the numbers to see if timing any elective procedures could help maximize your deductions.

Did anyone mention the "tiebreaker rules" yet? If both parents provide support and live with the child, the IRS has specific rules to determine who gets to claim the child: 1. First, parents can decide between themselves (if both qualify) 2. If they can't agree, it goes to the parent with whom the child lived the longest during the year 3. If the child lived with both equally, it goes to the parent with the higher AGI 4. If neither is a parent, it goes to the person with the highest AGI Just don't both try to claim the same kid or file HOH based on the same qualifying person. That's a quick way to get matching CP87 notices and have to prove who's right!

I see a lot of good advice here, but let me add one important point that might help with your decision-making process. Since you mentioned the potential $1,500 difference vs. having to pay $250, you should definitely run the calculations both ways to see your combined household benefit. However, I want to stress what others have mentioned about the separation issue - checking that box when you actually live together is considered tax fraud, not just a "gray area." The IRS defines separated as living apart with the intention of divorce or separation. Living together while unmarried doesn't qualify, regardless of your relationship status. For unmarried parents living in the same household, the general rule is that you can mutually agree who claims the child, but only that person gets to file Head of Household and claim all the child-related credits. The other parent must file Single. Make sure whoever has the better overall tax situation (considering income levels, other deductions, eligibility for credits like EITC) is the one claiming your daughter. If you're unsure about the calculations, consider using tax software that lets you model different scenarios, or consult with a tax professional who can run the numbers both ways safely and legally.

Don't forget to check if either partner had a negative capital account before the final distribution! This can create unexpected tax consequences. If one partner's capital account went negative during operations (meaning they took out more than they put in plus their share of profits), that negative balance is treated as income to that partner when the partnership dissolves. Also, make sure you file Form 8594 (Asset Acquisition Statement) if the partnership is selling any assets as part of the dissolution. And don't forget to file Form 966 to formally dissolve the entity with the IRS.

One more thing - check if either partner had any unreimbursed business expenses (UBE) they paid personally. These can be reported on Schedule E of their personal returns rather than being treated as capital contributions on the K-1. This is often better tax treatment since capital contributions don't directly reduce tax liability but UBEs can.