But that assumes you'd otherwise be working during that time. If you're doing taxes on a weekend when you'd just be watching Netflix anyway, isn't the calculation different?

You make a fair point about the weekend time value! I hadn't considered that angle, and you're right that if it's time you wouldn't be earning money anyway, the calculation changes. My main point was just to be mindful that sometimes we focus so much on saving the prep fee that we don't consider the value of our time or potential mistakes. But for a simple return like OP described, I agree it's likely worth it regardless of when you do it.

I've used FreeTaxUSA for 3 years now and love it. Federal filing is free and state is like $15. Interface isn't as slick as TurboTax but it does everything you need. I have W-2, mortgage interest, and retirement contributions too - worked great.

Wait seriously? So even if they approve my extension request, I'm still on the hook for late penalties for not getting them to the contractors by 1/31? That's not what I was expecting at all.

Yes, that's correct. The extension for 1099-NEC forms only applies to the portion you file with the IRS, not the requirement to furnish copies to recipients by January 31. This is different from some other tax forms, and it confuses many business owners. The recipient copies were legally required to be delivered by January 31 regardless of any extension. This is because the recipients need this information to accurately prepare their own tax returns. However, documenting your reasonable cause (the employee turnover) is still important, as it may help reduce penalties through a penalty abatement request even though it won't eliminate them entirely.

The IRS rarely hits people with the "intentional disregard" penalty though - that's usually reserved for repeat offenders or when there's evidence you were deliberately trying to avoid your obligations. As long as you're making a genuine effort to correct the situation now, you'll likely just face the standard penalties.

Thanks for pointing this out! My wife does have an SSN since she's been working with her F1 OPT. Do you know if making this election means we'd have to keep filing jointly every year going forward? Or can we choose differently next year?

That's good she already has an SSN - that will make the process much smoother. Regarding future years, the election remains in effect for all future tax years until it's terminated. You can terminate it in several ways: either spouse can revoke it by filing a statement, it automatically terminates if either spouse dies, you get legally separated under a decree of divorce or separate maintenance, or the IRS can terminate it with notice to either spouse if they determine that information to determine tax liability is inadequate. So yes, you're essentially committing to joint filing going forward unless one of those termination events occurs. That's why it's important to consider the long-term implications before making the election.

I tried doing this in TurboTax last year and it was a nightmare. It technically can handle it, but you have to know exactly what you're doing. The software doesn't really guide you through the 6013(g) election process clearly. For the capital gains, you can manually enter them in TurboTax, but again, you need to know exactly where to put everything.

Do you think this rises to the level of actual fraud though? I mean, she did provide incorrect information, but is misreporting health insurance coverage really something they prosecute for? I'm trying to gauge how serious this is.

It likely wouldn't rise to the level of criminal prosecution unless there were other serious issues with the return. The key distinction is between a mistake and willful misrepresentation. If she knowingly provided false information, that technically constitutes fraud, even if the direct financial impact is minimal. That said, for just health insurance misreporting without tax impact, the practical risk is relatively low. The IRS has limited resources and focuses enforcement on cases with significant revenue impact. Still, the safest approach is filing an amended return with the correct information to avoid any potential issues.

That's a really good point. I had a completely accurate return last year that took over 8 weeks, and I got no explanation. My friend filed the same week and got his refund in 10 days. The systems seem pretty random sometimes.

22 Do you need to go to the post office for certified mail or can you do it online somehow? I'm trying to avoid standing in those crazy post office lines.

7 You do need to go to the post office for certified mail, unfortunately. There's no way to do it completely online since they need to give you the tracking receipt in person. But here's a tip - you can use the USPS website to pre-fill all the certified mail forms and pre-pay, then just drop it off at the counter. Much faster than waiting in the regular line. If you absolutely can't make it to the post office, you could use a private service like UPS or FedEx which also provides tracking, and you can schedule those pickups online. Just make sure you're sending it to the correct IRS mailing address if you use a private delivery service.

13 You can also save the PDF versions to your computer instead of printing them, right? That's what I usually do.