Thank you for mentioning this option. I had no idea tax debt could be discharged through bankruptcy. Is that something that applies to all types of tax debt or just income tax? And did it affect your credit score as badly as people say?

Bankruptcy can only discharge income tax debt, not payroll taxes, fraud penalties, or certain other types. The debt needs to be from a return that was due at least 3 years ago, filed at least 2 years ago, and assessed by the IRS at least 240 days ago. Yes, bankruptcy did impact my credit score - it dropped about 150 points initially. However, it's already started recovering, and the relief of not having that massive tax debt hanging over me was worth it. I've been able to start rebuilding my credit, and some lenders actually see me as a better risk now because my debt-to-income ratio is so much better without the tax debt. I recommend at least having a consultation with a bankruptcy attorney who specializes in tax issues. Many offer free initial consultations, and they can tell you exactly which portions of your tax debt might be dischargeable.

Were you able to get your penalties reduced too? I've heard the IRS sometimes gives "first time abatement" but wasn't sure if that applies when you've already been on payment plans.

This is such an important distinction! I messed this up one year and it was a nightmare to fix. Quick question - if you have access to both an HSA and FSA (limited purpose FSA), can you contribute to both in the same year? My benefits coordinator gave me conflicting info.

Yes, you can contribute to both an HSA and a Limited Purpose FSA in the same year. The key is that it must be a "Limited Purpose" FSA that only covers dental and vision expenses, not a regular medical FSA that covers all healthcare expenses. Regular medical FSAs would make you ineligible for HSA contributions, but the Limited Purpose FSAs are specifically designed to work alongside HSAs. This combination actually gives you the most tax advantages, as you can use the Limited Purpose FSA for immediate dental/vision needs while letting your HSA investments grow for future medical expenses.

The limits for 2024 are higher just fyi: - $4,150 for individual coverage - $8,300 for family coverage Plus still the +$1,000 for 55+ folks

Is the contribution limit per calendar year or plan year? My company's health plan runs July-June but taxes are Jan-Dec. Always confuses me when figuring the max I can contribute.

Wouldn't using a credit card work too? Especially if you can get one of those 0% intro offers? My tax bill is much smaller than OP's but I was thinking of going this route.

Credit cards can work for smaller amounts, but there are a few things to consider. First, most credit cards charge a processing fee (usually around 2-3%) when paying taxes. Second, those 0% intro offers typically only last 12-18 months, and $48,000 would be hard to pay off in that timeframe. If you can't pay it off before the promotional period ends, you'll get hit with much higher interest rates than what the IRS charges. For smaller tax bills, credit cards with promotional rates can definitely make sense if you have a solid plan to pay it off before the promotional period ends. Just make sure to calculate the processing fee into your total cost comparison.

You're thinking of an Offer in Compromise (OIC), which allows you to settle your tax debt for less than the full amount. However, it's not as easy as people think. The IRS only accepts an OIC if they genuinely believe they can't collect the full amount from you, either now or in the future. They'll look at your income, expenses, asset equity, and ability to pay. Most OICs get rejected because people have the means to pay through an installment agreement. If you have assets you could sell or a decent income, it's unlikely to be approved.

That's an excellent point I hadn't considered. So even if I'm able to zero out my income tax through 401k contributions, I'd still be paying unnecessary SE tax if I don't claim my business expenses. Could you explain a bit more about how the SE tax calculation works with Solo 401k contributions?

Exactly! Solo 401k contributions don't reduce your self-employment tax liability - only your regular income tax. SE tax is calculated on your net earnings from self-employment (Schedule C profit) before any retirement plan contributions. So if you have $19,500 in income and don't deduct that $4,000 in expenses, you'd pay SE tax on the full $19,500. But if you properly deduct the $4,000, you'd only pay SE tax on $15,500. At the 15.3% SE tax rate, that's a savings of about $612. That's real money you'd be leaving on the table by not claiming legitimate expenses!

Did you get audited or have any issues with the IRS over it? I've been wondering how they would even know if you didn't report some expenses.

That's really good advice! What kind of documentation would be acceptable for cash jobs? Most of his work is for neighbors who just pay cash, no invoices or anything formal.

For cash jobs, create your own simple invoice system - even a notebook where you write down the date, customer name, service provided, and amount paid is better than nothing. Some people use apps like Square or PayPal for small jobs which automatically creates a record. The key thing the IRS wants to see is consistency and reasonableness. If you can show a regular pattern of work and income that matches the lifestyle you report on your taxes, that goes a long way. For expenses, keep ALL receipts for anything related to the work. Home improvement stores, gas, work clothes, tool repairs - these can all potentially be deductible depending on how they're used. Just make a note on each receipt what job it was for.

Self-employment tax is currently 15.3% of net earnings (12.4% Social Security + 2.9% Medicare). On $4,000 of net income, that would be about $612 in self-employment tax. However, you can deduct half of that on your 1040, which slightly reduces your income tax. But remember, you'll likely have deductible expenses that reduce your net income. If your husband spent money on tools, supplies, transportation to jobs, etc., those costs can lower the taxable amount significantly. Sometimes with proper expense tracking, the taxable income might be much lower than the gross income.

Thanks! That's helpful to know. I didn't realize I could deduct expenses against that income. I was worried about owing a big chunk of that $4k, but if I can deduct the gas, tool repairs, and other expenses, it might not be so bad.