Is there any disadvantage to filing an amended return if you do find a mistake later? I'm worried I might miss something when I switch platforms.

Filing an amended return isn't the end of the world, but it comes with several disadvantages. It can delay any refund you're expecting by several months since amended returns can't be e-filed and must be processed manually. The IRS is still working through a massive backlog, so paper processing times are extremely long. Amended returns also have a slightly higher chance of triggering additional review or verification from the IRS, though this isn't necessarily an audit. Plus, there's the hassle factor of having to go through the whole process again and potentially paying more fees to your tax software provider for the amendment service.

I've used both. FreeTaxUSA is way cheaper, but H&R Block definitely has a more polished interface. FreeTaxUSA asks more direct tax-form related questions rather than the conversational style of H&R Block. The end result is the same though - I've never had issues with either one calculating my taxes incorrectly. The biggest difference is that FreeTaxUSA charges like $15 for state filing while H&R Block charges $37+ depending on complexity. Federal is free with FreeTaxUSA for most situations. No audit protection included with the base package though, that's extra.

That's a great point I hadn't considered. We're in Oregon. Does anyone know if Oregon generally follows federal guidelines on settlement taxation or if they have their own rules?

Oregon generally follows federal treatment for physical injury settlements, so if your portion qualifies as tax-exempt under federal rules, it should also be exempt from Oregon state income tax. However, the key is still getting clarity on whether your guardian portion maintains the same character as the physical injury settlement. If the federal determination is that it's taxable as guardian fees, Oregon would likely treat it the same way.

This is definitely the best advice. I'm a paralegal at a firm that handles injury cases, and we always make sure to include specific language about tax treatment of guardian portions. If your attorney didn't do this, they really should have.

Wait, so even income my wife earned in her home country BEFORE getting her green card would count? We'd have to pay US taxes on that too? That seems unfair since she wasn't even a resident then!

Yes, that's exactly right. When you make the 6013(h) election, you're choosing to be treated as US residents for the ENTIRE tax year. This means all worldwide income from January 1st onward is subject to US tax reporting requirements, even income earned before your wife physically became a resident. It can seem unfair, but the trade-off is that you get to file jointly, which often saves significantly on taxes overall. You may also be eligible for the Foreign Tax Credit if she paid taxes on that income in her home country, which can offset any US tax owed on the foreign income.

TurboTax can handle it but not super smoothly. You'll need to manually attach the election statement. I used TurboTax last year for this exact scenario and had to write up the statement separately. The premium version did walk me through the dual-status alien questions though!

Does this work if my employer has me working from home 3 days a week? Or is it only for self-employed people?

Unfortunately, it's currently only available if you're self-employed or run your own business. W-2 employees working from home (even full-time) can't take the home office deduction anymore after the Tax Cuts and Jobs Act of 2017. Before 2018, W-2 employees could deduct unreimbursed business expenses (including home office costs) as miscellaneous itemized deductions, but that provision was suspended until 2025. If you're working remotely as a W-2 employee, your best option is to ask your employer about expense reimbursement programs instead of looking for tax deductions.

I actually think it depends on where you live. In high-tax, high-cost areas (California, New York, etc.), the mortgage interest and property taxes can be substantial enough to make itemizing worthwhile. In my case (Bay Area), my property taxes alone are over $18k, so combined with mortgage interest and charitable giving, itemizing saves me several thousand dollars compared to the standard deduction.

Is this worksheet approach better than using the online calculator? I'm always wary of the IRS online tools after they messed up my stimulus payment calculation.

The online calculator is generally more accurate than the worksheet because it can make more precise calculations based on your specific situation. The worksheet uses more generalized tables and might slightly over-withhold. I usually recommend people use the online calculator first, but the worksheet is helpful if you want to understand the methodology behind the calculation or if you're uncomfortable putting your detailed financial information into an online tool. Both approaches will get you close to your target, but the online calculator typically gets you closer to exactly breaking even.

This is really good advice. Last year we tried to hit zero exactly and ended up owing $800 because I got an unexpected bonus in December that pushed us into a slightly higher bracket.