Wait, employers can match 529 contributions? I had no idea that was even a thing! Is that common? My HR department never mentioned anything like this when going over benefits. Do you work at a large company or something?

It's definitely not as common as 401k matching, but it's becoming more popular as an employee benefit, especially at larger companies and in industries competing for talent with families. About 11% of employers offer some form of 529 contribution or matching now. Ask your HR department specifically about education benefits - sometimes they don't promote it well or it might be buried in your benefits handbook. Even smaller companies sometimes offer this benefit. Mine started it last year as part of a "family-friendly" initiative. The company contribution is considered taxable income for federal purposes, but the tax credit/deduction on your personal contribution still applies.

Great question about Ugift! In most states, only the account owner (you) can claim the tax benefits for 529 contributions, regardless of who actually contributes the money. That means gifts from family members to your child's 529 through Ugift typically won't qualify for anyone's state tax deduction or credit. However, a few states (like Colorado and Virginia) have special provisions allowing non-account owners to claim deductions for their contributions. Your family members would need to check their own state's rules if they're hoping for tax benefits.

Do you have to request a new PIN every year or does the IRS automatically send it? I'm worried about forgetting to get a new one.

The IRS automatically sends you a new IP PIN each year - you don't need to request it. They typically mail it in a letter around December or January before tax season starts. If you've created an online account with the IRS, you can also retrieve your current IP PIN there if you misplace the letter.

Were you able to get your refund back from the fake returns? I've heard horror stories about people waiting months or even years to get their money.

Is there a specific form or documentation the IRS sends to confirm they received your extension? I'm planning to file one for the first time and want to make sure I have all the proper documentation.

The IRS doesn't typically send a confirmation specifically for Form 4868 extensions. When you e-file the extension, you'll get a confirmation from whatever system you use (IRS Free File, tax software, etc.) showing it was accepted. This acceptance confirmation is your proof. If you make a payment with your extension, you'll get a separate payment confirmation. Save both of these confirmations - the extension acceptance and the payment receipt. I recommend saving them as PDFs and also printing physical copies. If you mail your extension, definitely send it certified mail with return receipt requested so you have proof of when it was delivered.

Technically, if you're getting a refund, you don't NEED to file an extension. The penalties for late filing only apply if you owe money. However, I still recommend filing the extension for two reasons: 1. If your calculations are wrong and you end up owing even a small amount, you'll be subject to late filing penalties if you didn't file an extension. 2. Some states require you to file a state extension even if you're getting a federal refund, so filing the federal extension covers your bases.

Thanks for the explanation! That makes a lot of sense. I think I'll file the extension just to be safe, even though I'm pretty sure I'm getting a refund. Better not to risk it in case my calculations are off.

Thanks for this suggestion! She does have a visa stamp in her passport. Are you saying we could use the visa number in place of an ITIN? I had no idea that was an option. Do you just enter the visa number where the tax form asks for the spouse's SSN/ITIN?

Not exactly - I should have been more clear. You can't use the visa number on the actual tax forms in place of an ITIN/SSN. What I meant was that for certain purposes (like opening bank accounts), sometimes the visa number can be used temporarily. For tax filing, you'd still need to follow one of these approaches: 1) Get the ITIN by submitting the W-7 with your return, 2) File as "married filing separately" now and amend later when you get the ITIN, or 3) File for an extension to give yourself more time to complete the ITIN process. Sorry for any confusion!

Did you need a professional translation service for the driver's license or just a certified translator? My wife has a Japanese driver's license but I'm not sure how to get it properly translated for the IRS.

Did you find it difficult to set up QuickBooks initially? I've heard mixed things about how user-friendly it is. Also, does it handle the LLC specifics well?

QuickBooks has a bit of a learning curve at first, but it's not too bad for a basic setup. I watched a couple YouTube tutorials and got comfortable with it in about a week. The mobile app is actually pretty intuitive for day-to-day stuff like taking pictures of receipts and tracking mileage. For LLC specifics, it handles the basics well for a single-member LLC (which is taxed as a sole proprietorship by default). If you have a more complex LLC setup with multiple members or special tax elections, you might need QuickBooks Online rather than Self-Employed. The main thing is that it keeps your business finances separate and organized, which is crucial for any LLC regardless of tax treatment.

I've been using TurboTax Home & Business for my LLC for 3 years now and it's actually pretty good. It walks you through all the business deductions and asks a ton of questions to make sure you don't miss anything. Costs around $170 for federal and state filing, which is way cheaper than a preparer.