Do NOT skip filing!! I did that for 2 years when I first started freelancing and it was the worst financial mistake ever. By the time the IRS caught up with me (they always do), my original $4k tax bill had ballooned to over $9k with penalties and interest. Plus they can hold your future refunds, put liens on your property, and even levy your bank accounts if you ignore them long enough. The stress of wondering when they'd come knocking was horrible. Just file and set up a payment plan - it's super easy online and the minimum payment can be as low as $50/month depending on how much you owe. Way better than the alternative!

Another option nobody's mentioned - you could file your taxes on time but pay with a credit card. The processing fee is around 2%, which is probably less than the IRS penalties would be. Then you can continue with your debt payoff strategy while avoiding IRS penalties. Not ideal to add to credit card debt, but if you're close to paying off your cards anyway and the interest rate on the remaining one isn't terrible, it might be mathematically better than IRS penalties + interest.

Your tax changes sound good, but don't forget to look at your state withholding too! I made the mistake of only adjusting my federal withholding when I got a raise last year, and ended up owing $1,200 to my state while getting a federal refund. The W-4 changes don't automatically adjust your state withholding in many states.

Has anyone actually tried doing a projection with real numbers? I'm in a similar situation and wondering if I should pay someone to do this or use one of those tax planning spreadsheets I see online.

Check Box 7 on your 1099-R! That's the distribution code and it determines how the withdrawal is taxed. If it's code "G" for example, it means it was a direct rollover to another retirement account and not taxable. Also look at Box 2a to see if there's a taxable amount. If it shows $0, that might explain why TurboTax is saying you don't need to report it (though you still need to include the form on your return even if the taxable amount is zero).

Has anybody else noticed TurboTax has been extra glitchy this year? I had a similar issue with my 1099-R where it kept telling me conflicting things about when to file it. Ended up switching to FreeTaxUSA and everything worked fine there.

One angle you might want to consider is having the foreign partner's LLC elect corporate status (Form 8832) AND then have that corporation qualify for benefits under an applicable tax treaty. Depending on the foreign partner's country of residence, this might reduce withholding rates. For example, if your foreign partner is from a country with a favorable tax treaty with the US (like the UK), a properly structured corporation might qualify for reduced withholding rates on certain types of income. However, this gets complicated fast because you need to consider: 1) Corporate tax at the US entity level 2) Withholding on distributions to the foreign owner 3) Branch profits tax considerations 4) Potential for treaty shopping challenges from the IRS

I tried something similar a few years ago with a German partner in our consulting firm. We created a Wyoming LLC owned by the German individual, and had it be the official partner in our partnership instead of the German person directly. Our tax advisor initially thought this would work, but then we got a notice from the IRS saying we still needed to withhold under Section 1446 because the LLC was a disregarded entity. We ended up having to file amended returns and pay penalties and interest for the missed withholding. The IRS specifically cited Treasury Regulation 1.1446-3 which basically says they look through disregarded entities to the ultimate owner for withholding purposes. So based on my expensive lesson, your idea probably won't work unless the LLC elects to be treated as a corporation.

I work at a university international student office and see this EXACT situation at least 5 times every tax season. International students/scholars get terrible advice from "recommended" preparers who claim false credits. DO NOT PAY THIS PERSON. File your amended return correctly, specifically noting that the original was filed incorrectly by the preparer without your knowledge or consent. Include Form 8275 (Disclosure Statement) with your amended return explaining the situation in detail. For future reference, many universities offer free VITA (Volunteer Income Tax Assistance) programs that specialize in nonresident tax returns. Many can help remotely even if you're no longer in the US.

Regardless of what you do with the IRS, make sure to file a complaint with your state's board of accountancy if the preparer is a CPA. If they're an enrolled agent, report them to the IRS Office of Professional Responsibility too.