Is there any way to tell TurboTax to be more consistent? Like maybe a setting to always include explanations or something? I'm preparing returns for multiple family members and it would be easier to explain if they all had similar structures.

Nah, not really. The tax software has to include certain forms based on specific tax situations - there's no override for that. The IRS expects specific forms for specific situations, and the software complies with those requirements. For the explanation worksheets, those are typically included based on automated triggers within the software. TurboTax might include more detailed explanations when amounts are close to thresholds or when there are multiple factors affecting a calculation.

Yes! The desktop version tends to include more supplementary worksheets and explanations. I've used both and the desktop version consistently produces longer returns with more supporting documentation. I think it's actually a feature of the desktop version since it's marketed more toward complex situations.

I've heard about OIC but wasn't sure if I'd qualify. Do they look at your assets too? I own my house with some equity in it and have a couple of vehicles. Would that disqualify me?

Yes, they absolutely look at your assets. The IRS typically expects you to liquidate or borrow against assets with equity before they'll approve an OIC. They calculate your "reasonable collection potential" based on your income, expenses, and asset equity. For your home, they'll consider the quick sale value (usually 80% of market value) minus any mortgages and exemption amounts. For vehicles, they'll look at equity beyond what's needed for basic transportation. Having assets with equity doesn't automatically disqualify you, but you'll need to account for that equity in your offer amount.

I got a Partial Payment Installment Agreement (PPIA) last year. It's definitely easier than OIC but still required full financial disclosure with Form 433-F. The key difference is that with PPIA, you make payments based on what you can afford until the collection statute expires (usually 10 years from assessment). After that, the remaining balance is forgiven.

Do you ever help families set up the payroll stuff? My nanny keeps saying she wants to be "on the books" but neither of us know where to start.

I don't personally set it up for families, but I do point them toward resources. Many use household payroll services like HomePay, SurePayroll, or Poppins Payroll that specialize in nanny taxes. They handle all the paperwork, tax withholding, and filings for around $40-60/month. I also recommend they check the IRS Publication 926 (Household Employer's Tax Guide) which explains everything. Most families find that once they have a system set up, it's pretty easy to maintain and gives everyone peace of mind.

This whole thing sounds so complicated and expensive. Is it really worth doing all this for a part-time nanny? How much extra does it end up costing?

That's a great point about the tax software! Which software are you using that gives you trouble with blank 199A sections? I'm using ProSeries right now.

I've had this issue with both UltraTax and Lacerte in previous years. ProSeries is actually a bit better about this particular situation, but you might still get a "soft" warning that you can override. For ProSeries specifically, you can usually bypass these warnings without entering zeros, but I've found that checking the box that says "QBI Not Applicable" in the 199A section often prevents the warnings altogether. The software is getting better each year at recognizing these situations, but it's still not perfect.

This is correct! I just checked the draft instructions for 2023 and they maintain the same guidance. There's a checkbox specifically for "all partners are C-Corps" that needs to be marked, but then you can skip the rest of the 199A calculations.

Does the ordering matter? Like what if I have both short-term and long-term losses carried over, and both short-term and long-term gains this year? Is there a specific way these have to be applied?

Yes, the ordering definitely matters because it can affect your tax rate. The IRS has specific rules for how losses and gains are netted against each other. First, short-term losses offset short-term gains, and long-term losses offset long-term gains. Then, if you have net losses in one category and net gains in the other, those net figures are used to offset each other. This is important because short-term gains are taxed at your ordinary income rate, while long-term gains get preferential tax rates.

You're absolutely right. You have to actually sell the investment (realize the loss) to claim it on your taxes. Holding onto stocks that have gone down in value doesn't create a tax loss you can claim - it's only when you sell them that the loss becomes "realized" and can be used on your tax return.

Thanks for confirming! That explains why I couldn't find any loss carryover from last year. At least i'll be able to use this year's losses to offset the gains I had earlier in the year, plus the $3000 against regular income.