Wait that's insane! So if I negotiate with my credit card company to settle a debt for less than I owe, I'd have to pay taxes on the amount they forgive? How would that even work with the timing? Like would I get a tax form the next year?

Exactly! The credit card company would send you a 1099-C form (Cancellation of Debt) in January/February of the following year showing the amount of debt that was forgiven, and you'd have to report that as income on your tax return. For example, if you settled a $15,000 debt for $10,000, you'd receive a 1099-C showing $5,000 of cancelled debt, which would be added to your taxable income. The timing can be especially brutal because by the time you get the form, you might have already spent that "savings" or not budgeted for the additional tax liability.

Your friend is partially right but for the wrong reason. The withholding calculations can be different between bi-weekly and monthly payrolls, but your actual tax liability at the end of the year is exactly the same regardless of pay frequency. What happens is that bi-weekly receives 26 paychecks per year (which equals 52 weeks), while monthly receives 12. The withholding tables sometimes calculate slightly differently, which can result in slightly different amounts being withheld. But when you file your actual tax return, it's based on your total annual income, not how frequently you received it.

Thank you for bringing this up! They don't have long-term care insurance unfortunately. They looked into Medicaid but were told they have too many assets to qualify right now. They're spending down their retirement savings at an alarming rate with these nursing home bills. Do you know if the medical expense deduction applies to withdrawals from retirement accounts that are used to pay for the nursing home?

Yes, you can still claim the medical expense deduction even if the money comes from retirement account withdrawals. The source of the funds doesn't affect the deductibility of the medical expense. However, be aware that withdrawals from traditional retirement accounts (like a traditional IRA or 401k) are generally taxable income, which will increase your AGI. This could potentially reduce the benefit of the medical expense deduction since you can only deduct expenses that exceed 7.5% of your AGI. It creates a bit of a circular problem - you withdraw money to pay medical bills, which increases your income, which raises the threshold for deducting those same medical bills.

Is there a good way to track all this? I've been keeping receipts in a shoebox but it's getting overwhelming.

This is incredibly helpful! When you worked with that CPA firm, did they give you a specific list of which states have those "factor presence" standards and what the exact thresholds are? That would be super valuable for me to have. Also, what do you mean by "responsive compliance"? Like, just wait until a state sends you a notice before filing there?

Yes, they provided a complete matrix showing all states with factor presence nexus standards. The key ones to watch are CA ($500k), NY ($1M), OH ($500k), WA ($267k for their B&O tax), and MA ($500k). But these thresholds change periodically, so you need to check current figures. By "responsive compliance," I mean exactly that - some agencies choose to file only in states where they clearly have nexus, and then respond accordingly if other states contact them. The reality is that states have limited resources to pursue out-of-state businesses, especially small service providers, so they tend to focus on larger targets first. It's a calculated risk approach rather than a strictly compliant one. Some CPAs advocate for this approach given the complexity, while others recommend full compliance with all potential nexus states regardless of practical enforcement risk.

Omg yes to the S-corp point! I got hit with penalties in NJ because my LLC (taxed as S-corp) didn't file there even though I filed my personal return with the flow-through income. Such a headache to sort out. Do u know if being a single-member LLC vs multi-member changes anything with the nexus rules?

19 Does TurboTax charge you if you start but don't file with them? I'm worried about paying twice.

14 TurboTax only charges when you actually file or print your return, not for just inputting your information. You can work through the entire process, see your estimated refund, and then decide not to file without paying anything. What I did was complete everything in TurboTax, printed out the draft forms (there's an option to print without paying), and took those to my CPA. This saved me money because the CPA spent less time gathering and inputting my basic information since I'd already organized everything.

22 Did you bring your previous year's return to the CPA? I've heard they can sometimes find mistakes from prior years too.

I had to start from scratch since there's no direct transfer between TurboTax and FreeTaxUSA, which was annoying but not the end of the world. Just had my previous year's return pulled up on my laptop for reference. The interface is definitely different - less hand-holding than TurboTax but still very straightforward. I found it actually asked fewer unnecessary questions. For your simple situation, I think you'd find it super easy. The whole process took me about 30 minutes for both federal and state. The biggest adjustment was getting used to a different layout, but the savings made it totally worth it.

I've used both. Cash App Taxes is good if you want completely free federal+state, but FreeTaxUSA has better support for certain tax situations. Cash App struggled with my HSA contributions and some investment stuff last year. FreeTaxUSA's interface is also more thorough in my experience - it asks more detailed questions that might help find deductions. But if your taxes are super straightforward and you want totally free, Cash App is fine.

Thanks for the comparison! I do have some investment accounts and started contributing to an HSA this year, so maybe FreeTaxUSA would be better. $12-15 for state isn't a big deal if it means a more accurate return. Might give it a try this year.