You should check your driver app accounts too. Even if DoorDash/UberEats didn't mail you a 1099, they sometimes have tax documents available for download in your driver portal. Worth checking before you file.

Don't forget you can deduct mileage for all those deliveries! Standard rate was 67 cents per mile for 2024. Even with just $475 in income, the mileage deduction could potentially offset most of that.

I'm confused about something. If I convert traditional IRA to Roth and have to pay taxes on that, isn't that considered a "capital gain" too since its investment money? So why can't capital losses offset it directly?

Just wanted to add a timing consideration that might help with your situation. Since you mentioned you're planning the Roth conversion "before year-end," you still have some flexibility here. If you haven't already realized those capital losses, you might want to consider the timing of when you actually sell those positions. You could potentially harvest some losses this year (say $10k) and save the rest for next year, then split your Roth conversion accordingly. This could give you more control over how much ordinary income you're adding each year and maximize the benefit of that $3k annual capital loss deduction. Plus, if you're close to a tax bracket threshold, this kind of planning could keep you from getting bumped up. Just something to think about as you're strategizing - the year isn't over yet so you have some room to optimize the timing of both the loss realization and the conversion.

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.

One thing nobody's mentioned yet - some states DO require S corporations to make estimated tax payments at the entity level, even though the federal government doesn't. For example, California requires estimated tax payments if your S corp will owe more than $500 in tax. New York has similar requirements. Make sure you're checking your specific state's requirements! I learned this the hard way last year and got hit with penalties.

Just a practical tip from someone who's had an S corp for 6 years - I set up a separate savings account where I transfer a percentage of all business income that passes through to me. This way I always have the cash ready for my personal quarterly estimated payments.

I'm wondering if anyone uses TurboTax? When I input bank bonuses without a form, it asks me to categorize them and I'm not sure which option to pick? There's "interest income" and "other income" and I'm confused which is right based on this discussion.

I went through this exact same situation two years ago with multiple banks. Here's what I learned from my tax preparer and subsequent research: 1. **Always report ALL income** - The $600 threshold only determines whether the bank must send YOU a form, but you're legally required to report all income regardless of receiving a form. 2. **Bank bonuses = Interest income** - These should be reported as interest income on Schedule B, not miscellaneous income. The IRS views these bonuses as compensation for letting the bank use your money. 3. **Keep good records** - Screenshot or save the promotional terms when you sign up for accounts. This helps you remember bonuses later and shows the IRS you're being diligent if questions arise. 4. **Pro tip**: Create a simple spreadsheet at the beginning of each tax year listing all your bank accounts and any bonuses you're expecting. I track the bonus amount, requirements (like minimum deposit), and whether I received a form. Makes tax time so much easier! The bottom line is that CITI should have sent you a 1099-INT since $300 is well above the $10 threshold for interest reporting, but their mistake doesn't eliminate your obligation to report it.