Thanks for these suggestions! Does the Bogleheads wiki cover the differences between holding foreign stocks directly vs through ADRs? That's the part I'm most confused about.

Yes, the Bogleheads wiki has a specific section comparing direct foreign shares vs ADRs from a tax perspective. They break down the pros and cons of each approach and even have country-specific guidance for major markets like UK, Japan, and Germany. They also have a great explanation of foreign tax "reclaim" procedures for when you're taxed at a higher rate than the treaty allows, which is common with direct foreign shares in some European countries.

I found Schwab's international tax guide super misleading though. It claimed I wouldn't need to file Form 1116 for any of their international funds, but then I got hit with excess foreign taxes that required the form. Better to rely on independent sources.

I hadn't even thought about checking with Social Security! Just created an account and looked at my earnings record. Thankfully nothing suspicious there yet - just my legitimate employer. Is there anything I should do with SSA proactively or just monitor it?

Just monitoring regularly is good since you don't see anything suspicious yet. If you do notice unexpected earnings in the future, you'll need to contact your local Social Security office and file a dispute. Since you haven't seen suspicious earnings yet, you're ahead of the game. My brother didn't catch his issue until tax time when his W-2 and SSA records didn't match. It was a nightmare to untangle, so checking early like you did is definitely the right approach!

Yes! Make sure to specifically request a "Letter 5071C" after you submit all your documentation. This is the IRS identity theft verification letter that confirms your case has been resolved. I keep copies of mine with my tax records just in case.

Did you have to include the full value of the house AND the full value of the note in the estate? Or was it just the house value minus the loan? The whole thing confuses me.

The estate included the house at its fair market value, and the loan was considered a separate asset of the estate (since it was money owed TO the deceased). So yes, both were included separately in the estate valuation. However, in practical terms, this meant the estate had the house (an asset) and the loan (also an asset from the estate's perspective, since it was money owed to my brother). Once everything transferred to me, the loan disappeared because I can't owe myself money. This is different from typical inheritance situations where the estate owes debts to third parties.

Could you explain more about the stepped-up basis part? If I inherit a house worth $500k but with $200k still owed on a loan I provided, what would my new basis be?

Venmo transactions can absolutely be used for business expenses, but your accountant is right to encourage using business cards when possible. The key with Venmo is documentation. Make sure to: 1) Use a business Venmo account separate from personal 2) Download monthly statements 3) Add notes to each transaction with business purpose 4) Take screenshots of the transactions Venmo doesn't automatically create detailed receipts like credit cards do, so you need to be more diligent about documentation.

Appreciate the straightforward answer! Just to confirm, so I should categorize it specifically as "Meals" rather than something more generic like "Supplies" or "Miscellaneous"? And you're confident this won't create any issues for my friend?

Yes, categorize it specifically as "Meals" because that's what it actually was. Using the correct categorization is always better than trying to hide something in a generic category. Remember that meals are still only 50% deductible (that temporary 100% deduction for restaurant meals expired). And I'm absolutely confident this won't create issues for your friend. Their tax obligations are completely separate from your expense categorization. The IRS doesn't have a system that flags "oh, this business claimed a meal from a non-registered business, let's investigate." Your friend needs to report their income regardless of how you categorize your expense.

Are meal deductions still a thing? I thought the Trump tax changes eliminated those, or reduced them significantly?

Business meals are still deductible, but it's now at 100% (temporarily increased from 50% during the pandemic, and Congress extended it through 2025). The key is that they need to be directly related to your business - like meeting with clients, potential customers, or business associates. You can't just deduct your lunch when you're working alone. The rules have changed several times in recent years, so it's worth double-checking current guidelines when you file. But yes, legitimate business meals are still deductible expenses.

That's only if you itemize deductions though, right? Most self-employed people I know take the standard deduction because it's usually higher unless you have a mortgage with lots of interest.