I have some experience with this. Indian REITs are still relatively new but from a US tax perspective, they don't get the same favorable treatment as US REITs. The distributions get taxed as ordinary dividends without the partial return-of-capital treatment that US REITs often have. Also, you'll face additional reporting requirements on Form 8621 if the Indian REIT is considered a PFIC, which many foreign investment structures are. This can result in much more complex tax filing.

Thanks for the explanation about the taxation differences. That's really helpful to know about the ordinary dividend treatment without the return-of-capital benefits. So it sounds like from a tax efficiency standpoint, I might be better off sticking with US REITs or finding a US-based ETF that gives exposure to the Indian real estate market rather than directly investing in Indian REITs. The Form 8621 filing requirement sounds like a headache I'd rather avoid.

TurboTax can handle the basic foreign tax forms like 1116, but I found it struggles with more complex situations involving PFICs and multiple types of foreign income. I switched to using a CPA who specializes in international taxation after TurboTax kept giving me errors for my Indian stock investments.

Thanks for the advice! We actually have a bunch of this stuff already - especially emails about schedules and very detailed instructions on how to complete tasks. There's also an employee handbook she had to follow despite being classified as a "contractor." Would it be helpful to include copies of these with the SS-8 form or just describe them?

You should definitely include copies of the most relevant documents along with your SS-8 filing. The employee handbook is particularly valuable evidence - that's a smoking gun that shows they treated her as an employee. I'd select the strongest 10-15 examples rather than overwhelming them with everything. Focus on documents that clearly show the company controlled how and when she worked, required her to follow specific procedures, or explicitly treated her as part of the company rather than an outside contractor.

This is terrible advice. Most employers know exactly what they're doing - saving themselves the employer portion of payroll taxes and avoiding labor laws. Approaching them directly just gives them a heads up that you're onto them and time to prepare a defense or even fire you.

Does the Multiple Jobs Worksheet account for capital gains at all? Or is there a different form for that? My situation is similar but I'm also getting rental income now.

The Multiple Jobs Worksheet doesn't account for capital gains or rental income at all. It only helps calculate withholding when you have multiple W-2 jobs simultaneously or when both spouses work. For capital gains and rental income, you should use Step 4(a) of the W-4 to add your estimated "other income" that won't have withholding. Alternatively, you can make quarterly estimated tax payments using Form 1040-ES, which is often better for irregular income like capital gains or rental income. The safest approach is to use the IRS Withholding Estimator online and update your W-4 whenever your income situation changes significantly.

I did something similar but estimated quarterly payments for my freelance income saved me from the penalty. For the OP - If you expect to owe more than $1,000 when you file, quarterly payments are the way to go.

Based on IRS rules, your boyfriend would need to file as Single, not Head of Household. To file as HOH, he would need a "qualifying person" who is either his qualifying child or qualifying relative. Since you're already using your child's SSN for EIC purposes, your boyfriend generally can't use the same child as his qualifying person for HOH status. This is a common issue in unmarried couples with children. Only one taxpayer can claim a specific child for purposes like this, and using the SSN for EIC essentially "locks in" that child to your tax return for these purposes.

Thanks for clearing that up! We've been doing it wrong for years then. Does this mean we should file amended returns for previous years? Or just start filing correctly going forward?

Not a dumb question at all! If they got married, they could file jointly which would eliminate the HOH issue entirely. Married Filing Jointly often provides better tax benefits than two separate returns (one HOH and one Single). When filing jointly, they could claim their daughter as a dependent (if she otherwise qualifies) and also claim EIC if they meet the income requirements. Married Filing Jointly sometimes has higher income thresholds for certain credits too. However, there can occasionally be a "marriage penalty" if both partners have similar high incomes.

Oh that's scary! I haven't been great about keeping receipts for my textbooks... do digital receipts from Amazon and the campus bookstore work too? And how long should I keep these records?

Digital receipts are absolutely fine! Just make sure they clearly show what was purchased (the book title), the date, and the amount. I recommend saving them as PDFs and keeping them in a dedicated folder on your computer or cloud storage. You should keep all tax-related records for at least 3 years after you file your return, since that's typically how far back the IRS can go for an audit. Some experts recommend keeping them for 6-7 years to be extra safe. My brother's audit happened about 2 years after he filed that return.

The felony drug conviction restriction was actually removed a few years ago! That's no longer a disqualifying factor for the AOTC as of the tax law changes in 2021.