11 Is there a minimum amount of tax debt for an Offer in Compromise to be worth it? I owe about $6,500 which is a lot for me right now but not like tens of thousands.

16 There's no minimum amount required for an Offer in Compromise, but the process is intensive enough that it's usually pursued for larger debts. For $6,500, a payment plan might be simpler unless you have extreme financial hardship. The IRS looks at your ability to pay, income, expenses, and asset equity. They essentially ask: "Could we reasonably expect to collect more from you over time than what you're offering now?" If your financial situation is truly dire with no improvement in sight, it could be worthwhile even for smaller amounts.

3 Would it make sense to put like half on a credit card (the amount I could pay off in 2-3 months) and then get on a payment plan for the rest? My tax bill is around $4300 and I could probably handle about $2000 on my card.

I've had good experiences with Track1099 for corrections. Their interface is really straightforward for amendments - there's literally a "create correction" button that walks you through the process step by step.

Thanks for the recommendation! I'll check out Track1099. QuickBooks has been a nightmare for this - it keeps wanting me to create new 1099s from scratch without any way to mark them as corrections properly.

Thanks for suggesting this. Do you know if taking out a loan would impact my credit score significantly? Mine's currently around 720 and I'm trying to save up for a house in the next year or two.

There would be a small initial dip when the lender does a hard credit pull, maybe 5-10 points. Then your score might drop a little more when the new account appears, reducing your average account age. However, if you make all payments on time, your score should recover within a few months and potentially go even higher as you demonstrate responsible payment history. The biggest risk to your score would be from missing payments on the loan, which would be much worse than the temporary dips from opening the account.

This is super important advice. I put off filing one year because I couldn't pay, and those failure-to-file penalties were brutal. Ended up owing way more than I would have if I'd just filed and set up a payment plan right away.

Would you mind explaining a bit more about those unexpected complications with California? I'm in a similar situation with a Delaware entity but live in California.

Sure thing. California takes the position that if you're a CA resident managing the holding company, they can tax the income and capital gains regardless of where the entity is formed. What happened in my case was that I had created a Delaware holding company owning several startup equity positions, but since I was making all investment decisions from California, the state considered it a California business. When I sold two of my positions for a significant gain, California required me to pay state tax on the entire gain, effectively ignoring the Delaware structure. I also had to deal with California's "doing business" fee since they deemed my holding company to be operating in California. The real surprise was that I still had to pay Delaware franchise tax while also being fully taxed by California - basically getting the downsides of both states without the expected benefits of Delaware.

That's actually a complicated area. You can use a Self-Directed IRA for certain equity investments, but there are prohibited transaction rules that can easily be violated with startup equity. If you're actively involved with any of the companies, it's especially problematic. Plus many equity compensation types like ISOs and NSOs can't be held in IRAs directly.

Theres also something called a "tie-breaker" rule in most tax treaties that helps determine which country gets primary taxing rights when both claim you. Usually comes down to where you have stronger personal connections, permanent home, etc.

You're absolutely right about the tie-breaker rules. They're crucial in these situations. Most treaties follow a hierarchy of tests: permanent home first, then center of vital interests (personal/economic connections), then habitual abode, and finally nationality. For a company, the tie-breaker often comes down to where the effective management is located - which in the original poster's case would likely be New Zealand since that's where the actual decision-makers are physically located, regardless of where the company is registered.

How much does an international tax accountant usually cost? I'm in a similar boat with income from three different countries and I'm terrified of getting it wrong, but also worried about the cost.