For someone in your situation with $475K from a business sale, I'd strongly recommend "The Tax and Legal Playbook" by Mark Kohler. He's both a CPA and attorney, so he covers both the tax optimization and asset protection angles really well. The book specifically addresses how to structure things after a liquidity event like yours. Another excellent resource is "Loopholes of Real Estate" by Garrett Sutton - even if you're not planning to invest in real estate, it explains how different entity structures work for asset protection in ways that apply to any type of wealth. One thing I learned the hard way: don't rush into setting up complex structures just because you can. Start with understanding what you're actually trying to protect against and what your ongoing tax situation will look like. Sometimes a simple LLC is perfect, other times you might need a more sophisticated setup with trusts or multiple entities. Also, make sure whatever accountant you work with has experience with business sales and the resulting tax implications. The person who did your personal returns might not be the best fit for post-sale planning.

Coming from a similar situation (sold my tech consulting business last year), I can't recommend "The Entrepreneur's Guide to Business Law" by Bagley and Dauchy highly enough. It's more comprehensive than most single-topic books and covers everything from entity selection to exit strategies. For the asset protection side specifically, "Asset Protection for Everyone" by Robert Mintz is written in plain English and doesn't assume you have a law degree. He explains when simple structures work versus when you need more sophisticated planning. One practical tip: before diving deep into books, spend a weekend mapping out your current financial situation, future income expectations, and what specific risks you're trying to protect against. This will help you focus on the most relevant sections of whatever books you choose. Also, since you mentioned feeling lost with your accountant - consider interviewing 2-3 different CPAs who specialize in business owners and wealth management. The right professional relationship will be worth more than any book, and they can recommend additional reading tailored to your specific situation.

Have any of you had luck with the Taxpayer Advocate Service? My cousin was in a similar situation but much more severe. They really helped him, and it's totally free!

I've been through something very similar with my elderly father who also had significant tax debt and language barriers. Here are a few additional thoughts based on what worked for us: Definitely go with Form 2848 as others have suggested - the full power of attorney is essential when dealing with complex cases like this. When you fill it out, I'd recommend being very broad with the tax years (maybe 2010-2024) and tax matters you're requesting authority for. This gives you maximum flexibility to address any issues that come up. One thing that really helped us was getting a complete Account Transcript from the IRS once the 2848 was processed. This shows every transaction, payment, penalty, and interest charge on the account going back years. It helped us identify some penalties that shouldn't have been applied and gave us the full picture of what we were dealing with. Also, don't overlook the possibility of an Offer in Compromise if your mom truly can't pay the full amount and is unlikely to be able to in the future. Given her age, fixed income, and the size of the debt, she might qualify to settle for much less than the full amount owed. The key is getting that 2848 filed first so you can start gathering information and exploring all the options available to her.

Something else to consider - location matters too! Some states offer state-level earned income tax credits to ITIN filers even when they're ineligible for the federal EITC. California, Colorado, Maryland, and a few others have inclusive state credits that can boost refunds for undocumented taxpayers with dependents.

This is a really comprehensive discussion! One thing I'd add is that documentation requirements can also create differences in practice. While both citizens and ITIN holders can claim dependents, citizens typically have easier access to required documents like Social Security cards for their children. For mixed-status families where some children are citizens and others aren't, the tax benefits can vary significantly per child within the same household. Citizen children with SSNs qualify for more credits than children without SSNs, even when claimed by the same parent. This creates complexity that many families don't realize until they're preparing their taxes. Also worth noting that some undocumented immigrants overpay taxes through withholding but don't file returns to claim refunds due to fear or lack of knowledge about their rights. The IRS estimates billions in unclaimed refunds each year, with a significant portion likely from immigrant communities.

I'm in this exact situation - our income jumped from around $180k to $240k and suddenly we owe instead of getting a refund! Has anyone tried adjusting withholdings to account for this? I'm thinking of changing my W-4 to withhold an additional $200 per paycheck to avoid owing next year.

I went through almost the exact same situation two years ago - income jumped from $165k to $225k and suddenly owed $800 when we'd always gotten refunds before. The shock is real! What helped me understand it was realizing that our 401k contributions were still doing their job (reducing taxable income), but we were losing other benefits I didn't even know we had. The student loan interest deduction completely disappeared at our new income level, and we lost some education credits for my spouse's graduate courses. The other big factor was that more of our income was now taxed at higher marginal rates. When you're at $175k vs $228k, a much larger chunk of that income falls into the 24% bracket instead of the 22% bracket. That alone can create a significant difference in your tax liability. I'd definitely recommend running the numbers on adjusting your withholdings for 2025. We ended up increasing our 401k contributions slightly and adjusted our W-4 withholdings to account for the higher tax burden at our new income level.

I wonder if it's worth trying a different tax software? I started with TurboTax and it said I had to mail my Oregon return, but when I tried FreeTaxUSA with the exact same information, it let me e-file with no problems. Could be worth the time to input your info elsewhere if you really want to avoid mailing.

Another thing to check is whether you're filing early in the tax season. I had this exact problem with Michigan a couple years ago - filed in late January and was forced to mail my return even though my situation was straightforward. When I called the state tax department, they explained that they sometimes disable e-filing for certain forms or situations at the very beginning of tax season while they're still testing their systems. The rep suggested I wait until mid-February and try again. Sure enough, when I re-submitted the same return information a few weeks later, it went through electronically with no issues. Might be worth holding off for a couple weeks if you filed very early, especially since you mentioned this hasn't been a problem in previous years.