Oh crap, I didn't even think about state requirements! I'm in California - does anyone know if I need to file something separate for my LLC at the state level?

California requires an automatic 6-month extension for filing your state personal income tax return, so you don't need to file a separate extension form for that. However, you still need to pay any estimated tax you owe by the original due date. For your LLC specifically, California requires an annual LLC tax of $800, which is due by the 15th day of the 4th month of your taxable year (April 15 for calendar-year taxpayers). This payment isn't extended by your personal extension, so make sure you've paid that already if it applies to you.

I've been using QuickBooks Self-Employed for my single-member LLC and it's been great for tracking everything. It even has a tax estimation feature that helps you set aside the right amount each quarter.

That's really helpful! I had no idea about Form 5471 or the GILTI tax issues. My LLC is basically dormant now - I just kept it because I thought I might move back to Canada someday. But sounds like the tax headaches aren't worth it. Is there anything specific I need to know about the dissolution process from a tax perspective? Will I face any kind of "exit tax" when dissolving it?

When dissolving a Canadian LLC, you'll need to make sure all its assets are distributed, which can trigger capital gains in Canada. The corporation will need to file a final tax return in Canada showing the disposition of all assets. From the US side, you'll need to report the liquidation on your personal tax return. Any assets you receive from the corporation above your basis could be taxable in the US. You'll also need to file a final Form 5471 indicating the dissolution. If the LLC has significant retained earnings or appreciated assets, it gets more complicated. In that case, definitely get professional help to structure the dissolution in the most tax-efficient way possible. But for a relatively simple or dormant LLC, the process is straightforward and the long-term tax savings are substantial.

The US tax system is absolutely ridiculous with these foreign account reporting requirements. My friend got hit with a $10k penalty for not filing an FBAR on a Canadian account with barely $12k in it. Meanwhile billionaires are using sophisticated tax shelters with barely any consequences.

It is frustrating, but the penalties are even worse if you ignore the requirements. The best approach is to get compliant as quickly as possible. The Streamlined procedures are still available for those who weren't aware of their filing obligations. The good news is that once you're in the system and filing regularly, it becomes routine. I now just keep a spreadsheet with my maximum account balances throughout the year and filing the FBAR takes about 20 minutes online. Form 8938 is more complex but most tax software handles it fairly well.

I didn't know about checking that box! Will that really help? And I don't have kids, so I'm not sure about the tax credits. I'm filing as single.

Yes, checking box 2(c) on the W-4 helps when you have similar-paying jobs. It basically tells your employer to withhold at a higher rate to account for your total income being higher. Even without kids, you might still qualify for EITC depending on your exact income. With your combined jobs totaling around $52,000, you might be just over the limit for a single filer, but it's worth checking. There are also education credits if you're taking any classes, or the Saver's Credit if you've contributed to a retirement account.

This is what I've been doing for years with multiple jobs. I have them take an extra $100 per paycheck from my main job. I'd rather get a refund than scramble to pay a bill in April!

This is super helpful! I hadn't even thought about the dependent thing. I am still living with my parents and they pay for most of my stuff, so I'll definitely check with them about this. Is there an easy way to calculate how much I should be setting aside each time I get paid? I'm making anywhere from $150-400 a week depending on how many gigs I pick up.

A simple rule of thumb is to set aside 30% of everything you earn. That should cover both your self-employment tax (which is about 15.3%) and your federal income tax. If your state has income tax too, you might want to bump that up to 35%. The easiest way to manage this is to open a separate savings account just for taxes. Every time you get paid, immediately transfer 30% to that account and don't touch it. At tax time, you'll have the money ready to pay what you owe. Plus, if you end up owing less than you saved, you'll have a nice little bonus!

This is so important! I got slapped with a $420 penalty my first year freelancing because nobody told me about quarterly payments. The IRS doesn't play around with this stuff.

Do the free fillable forms on the IRS website count as e-filing? That seems like a good middle ground where I could still fill everything out myself but submit electronically.

Yes, the free fillable forms definitely count as e-filing! That's exactly the perfect middle ground. You'll still need to understand each form and calculation yourself (unlike with TurboTax which handles that for you), but you get the benefit of electronic submission. This way you still get the educational experience of working through the forms manually, but avoid the massive delays of paper processing. Plus, the fillable forms will catch basic math errors, which is helpful when you're learning.

I've heard about that program before! Do you need any special qualifications to volunteer, or can anyone sign up for the training?