One thing to watch for on 1099-Rs that nobody mentioned yet - if you're under 59½ when you take distributions, you might see a "1" code in Box 7, which means you could be hit with an additional 10% early withdrawal penalty unless you qualify for an exception. This is on top of the regular income tax you'll pay on the distribution amount. There are exceptions to this penalty for things like first-time home purchases (up to $10k), certain educational expenses, disability, and some medical costs. But you need to make sure you claim these exceptions properly on your tax return using Form 5329.

Just a heads up, the 1099-R might also show state tax withholding in boxes 12-15 if applicable. Make sure you include this on your state return if you had state taxes withheld from your distribution! I forgot this last year and ended up amending my state return.

I had this same problem in 2023! The key thing to know is that you CANNOT file separate returns for different income sources. The US tax system requires one comprehensive return that includes ALL income sources. Here's what I did: 1) I used the same software I originally filed with (sounds like H&R Block for you) 2) Started an amended return (1040-X) 3) Added Schedule C for the side business income 4) Included Schedule SE to calculate self-employment tax 5) Paid the additional tax owed right away to minimize penalties Don't stress too much about it - this happens all the time, especially to people new to self-employment!

A heads up about timing - I filed an amended return last year and it took about 20 weeks to process! The IRS is seriously backlogged with amended returns. Make sure you keep documentation showing when you filed the amendment in case there are any questions about late penalties.

I'd just suggest checking what kind of CPA you're hiring. Not all CPAs specialize in individual taxes. I hired one last year who mainly did corporate taxes and he missed some pretty basic deductions that I caught myself later. Ask specifically about their experience with side businesses and home purchases. Also, see if you can find someone who offers year-round tax planning, not just tax preparation. The really good ones will help you make decisions throughout the year to optimize your tax situation for next year too.

Honestly, for what you described, you're in the sweet spot where a CPA is probably worth it THIS year, but you might be able to DIY again in future years. The first year with a house and business has lots of new tax situations that a CPA can help optimize, but once those are set up correctly, you might be able to follow the same patterns yourself. I did exactly this - paid for a CPA when my taxes got complicated, took detailed notes on what they did, and then used that knowledge to DIY the next year when my situation was stable.

Based on my experience as a dual US-Canadian citizen running a business, consider establishing a Canadian corporation if you're planning to stay in Canada long-term. Here's why: - Canadian corporate tax rates can be very favorable for small businesses (as low as 9% federal + provincial on the first $500K of active business income) - You can defer personal taxation by keeping money in the corporation - You still need to file US taxes as a citizen, but can use foreign tax credits - Your wife, as a non-US person, can receive dividends from the Canadian corporation that may not be subject to US taxation The downside is compliance costs - you'll need to file US FBAR, Form 5471 (for foreign corporations), and possibly deal with GILTI tax. But overall, the tax savings often outweigh these costs.

Just a warning from someone who went through this - don't forget about Social Security! As a US citizen in Canada, you'll be covered by the US-Canada totalization agreement. This determines which country's social security system you pay into. Generally, if you're self-employed and residing in Canada, you'd pay into the Canadian system (CPP) and be exempt from US self-employment tax. You need to get a certificate of coverage from the Canadian authorities to claim this exemption. This saved me about $15K in US self-employment taxes my first year abroad that my first accountant missed!

For what it's worth, I've used Direct Pay with a name change (after divorce, not marriage) and it worked perfectly fine. Like others have said, the verification is just checking that you are who you say you are based on previous tax information. Your SSN is what really matters - that's the unique identifier the IRS uses to track everything. Once you get through the verification step, you'll have the option to select what you're paying for. Just make sure you choose: - Form 1040 - Tax Year 2024 - Reason for payment: Payment with return As long as those are set correctly, your payment will be applied properly regardless of your name change or filing status change.

I work at a tax prep office (not an expert though, just admin) and this comes up ALL the time. The Direct Pay system is just using your previous return to verify your identity, but your actual payment gets applied based on the tax year and form type you select later in the process. Your SSN is the magic key that connects everything. As long as that hasn't changed (and it shouldn't!), you're good to go. Name changes, address changes, filing status changes - none of that matters for the payment application.