Can you explain more about this step transaction thing? If the kids become legitimate partners with economic risk, why would the timing matter? Seems like as long as they're real partners with real rights the IRS shouldn't be able to collapse anything?

The step transaction doctrine is an IRS principle that looks at the substance over the form of a series of related transactions. Even if each step is technically legal, if the IRS determines they were pre-planned steps to achieve a tax result that wouldn't be available if done directly, they can collapse them into a single transaction. For family LP transfers specifically, if you gift LP interests to your kids and then the partnership sells the property shortly after, it can appear that the only purpose of bringing them in was to split the capital gain among more taxpayers. This is especially true if there were discussions about selling before the transfer of interests. The key is establishing that each partner has legitimate economic risk and that the transfer of interests had independent business purpose beyond just tax savings. Documentation of meetings, legitimate business reasons for the transfers, and allowing time between transactions all help demonstrate these weren't just predetermined steps in a tax avoidance scheme.

Yes, a CRT can work with property held in an LP, but it gets complicated. The LP would typically distribute the property to the partners first, then the partners would contribute their interests to the CRT. The main benefit is you avoid immediate capital gains tax on the appreciation when the property is sold inside the CRT.

That sounds like a good option! How did you find them and was there a long wait time to get an appointment? I'm wondering if they're available year-round or just during tax season?

I found my local VITA site by using the IRS's locator tool on their website - just search "VITA locator IRS" and it should come up. The wait time varies depending on the time of year. During tax season (January-April), it can be 1-2 weeks for an appointment, but they often have walk-in hours too. Most VITA sites are only open during tax season, typically January through April 15th, with some sites remaining open until October for extension filers. A few larger sites in major cities operate year-round, but they're the exception. If you're outside tax season, you might want to call ahead to check if any sites in your area are still operating.

I used a Certified Acceptance Agent last year and it was worth every penny. Paid $150 but they handled everything - verified my documents, made sure my W-7 was filled out correctly, and submitted everything together with my tax return. Got my ITIN in about 6 weeks with zero hassle. Just make sure you find one that's actually IRS-authorized! You can check on the IRS website for legitimate CAAs.

Thanks for your input, but I'm actually dealing with a larger amount - the refund was around 3,800 CAD, and the exchange rate has changed enough that the loss is more than $300. I'd prefer to do things by the book, especially since I'm planning to apply for citizenship in a couple years and don't want any tax issues to complicate that.

Fair enough. For amounts over $200, it's probably worth reporting correctly. Just wanted to point out that sometimes the tax benefit isn't worth the extra paperwork, but in your case it makes sense to get it right.

That's actually a good point. I use the XE Currency app to track exchange rates and set alerts when they hit certain thresholds. CAD has been trending up a bit lately against USD compared to last year.

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.

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.