Oh snap, I didn't even think about state returns! I've lived in three different states over the last decade (moved for work a couple times). Does that mean I need to look up each state's rules?

Yes, you should check each state's rules where you've filed. The statute of limitations varies - California is 4 years, New York is 3 years, and some others have different timeframes. If you want to keep things simple without researching each state, just keep everything for 7 years. That covers the longest standard statute across all states and the federal extension for substantial underreporting. But if you're really tight on space, it's worth looking up the specific states where you filed.

Is that secure enough though? I'm worried about tax docs in the cloud. Wouldn't a local hard drive be safer?

That's a really good point I hadn't considered. Since I'm transitioning to W-2 soon, what's the best way to make sure enough is withheld? Should I just put "0" allowances on my W-4? And how much should I set aside from my remaining 1099 income for the rest of this year?

I'd recommend using the IRS Tax Withholding Estimator on their website to calculate exactly what you need for your W-4. With your student loans and other deductions, putting "0" might withhold too much and hurt your monthly cash flow when you're already tight. For your remaining 1099 income, the general rule is to set aside about 30-35% of your gross earnings for federal, state, and self-employment taxes. Since you're in a combined income situation with your husband's W-2, it gets more complicated, but that percentage should keep you safe. Make quarterly estimated payments on those earnings to stay compliant and avoid next year's penalties.

This is actually not entirely correct. The IRS can file a Federal Tax Lien even for amounts under $25k in some circumstances. Also, while being on a payment plan itself doesn't report to credit bureaus, if you default on your payment plan, it absolutely can impact your credit indirectly through collection actions.

It was an employment lawsuit - wrongful termination and some back wages. Does that change things? I'm still confused about whether I need to itemize to deduct the attorney fees or if I can take the standard deduction AND still deduct the attorney portion somehow.

That's actually good news! For employment-related lawsuits including wrongful termination, you can deduct your attorney fees as an "above-the-line" deduction. This means you can still take the standard deduction AND deduct your attorney fees. You'll want to look at Schedule 1, Line 24 "Other adjustments" and write "ATTORNEY FEES" next to it with the amount. This way you're not taxed on money that went straight to your attorney. Employment cases specifically have this special treatment thanks to a tax law change that was made specifically to address this unfair situation.

While I agree the tax code is complex, this isn't quite accurate. For employment-related cases (which OP mentioned in comments), the attorney fees can be deducted as an above-the-line deduction. Congress actually fixed this problem for certain types of cases, including employment claims, civil rights cases, and whistleblower claims specifically to prevent double taxation.

Is it too late to apply for a TCC for this filing season? We need to get this 1099 out pretty soon, and I'm worried about missing deadlines.

At this point in the filing season, it's probably too late to apply for a TCC for the current year. The IRS typically takes several weeks to process TCC applications, and we're already close to the January 31 deadline for issuing 1099s. I'd recommend going with one of the third-party e-filing services for this year. They're affordable for just one form and will ensure you meet the deadline. You could apply for a TCC later this year if you expect to be filing 1099s again next year.

The threshold for issuing a 1099-MISC for rent payments is $600. So if you paid the property owner at least $600 in rent during the year, you're required to issue a 1099-MISC with the amount reported in Box 1 (Rents). This is separate from the threshold for independent contractors, which is also $600 but would be reported in Box 3 instead. Since you're paying rent to a property owner, Box 1 is the appropriate place to report it.

I've been considering that switch actually. Do you know if there's an optimal balance between Roth and traditional contributions for someone with variable income? My base salary is pretty consistent but these commission checks can range wildly from $5k to $20k depending on the month.

For highly variable income like yours, many financial advisors suggest a hybrid approach. Use traditional pre-tax contributions during your high commission months to reduce the tax hit when you're temporarily pushed into higher brackets. Then use Roth contributions during lower income months when you're in a lower tax bracket. The general principle is to make traditional contributions when you're in a higher bracket than you expect to be in during retirement, and Roth contributions when you're in a lower bracket. With your variable income, you're effectively moving between brackets throughout the year, so you can strategically use both types of contributions.

I adjusted mine last year for my sales commissions. Put $200 on line 4(c) for reduced withholding. Ended up about right at tax time - got a small refund of $300. You have to be careful though and maybe do some math based on your total expected annual income. The IRS has a tax withholding estimator on their website that's pretty helpful.