I think everyone's missing an important point here - you should check with your HR department about why this change happened! I had something similar occur and it turned out my employer had been putting money in the wrong account all year. I had to get that fixed before I could file correctly.

This thread has been incredibly helpful! I'm dealing with a similar situation where my W-2C changed a Box 12 code from D to W, but I also noticed the amounts don't quite match what I thought I was contributing throughout the year. Based on what everyone's shared here, it sounds like I should definitely contact HR first to understand exactly what happened with my contributions before filing. The last thing I want is to file correctly according to the W-2C but then discover there's still an underlying issue with where my money actually went. Has anyone else had experience where the W-2C was correct for tax filing purposes but there were still account corrections needed on the employer's end? I'm worried I might have money sitting in the wrong account type even though the tax reporting is now fixed.

Don't forget about FATCA and FBAR requirements! When you have financial accounts outside the US exceeding certain thresholds, you need to report them. FBAR (FinCEN Form 114) is required if your foreign accounts exceed $10,000 at any point during the year, and FATCA forms are required at various thresholds depending on your filing status. The penalties for not filing these forms are CRAZY high even if you don't owe any tax. Like, $10,000+ for non-willful violations. Make sure you're tracking all your NZ bank accounts, including any business accounts for that B&B venture.

Just wanted to add another perspective on the business structure aspect. Since your wife would be the owner of the B&B as a NZ citizen, you'll also need to consider whether this creates any issues with US gift tax rules if you're contributing funds to a business you don't legally own. Also, regarding the rental property in the US - even if you're breaking even cashflow-wise, don't forget that you'll be taking depreciation deductions which will reduce your basis. When you eventually sell, you'll have depreciation recapture to deal with, which is taxed as ordinary income up to 25%. This could create a significant tax bill down the road that many people don't anticipate. One more thing to research: NZ has something called the "bright-line test" for property investments, which could affect the tax treatment of your B&B if you sell within a certain timeframe. Since you're planning to reinvest profits initially, this might not be immediate concern, but it's worth understanding for long-term planning. The international tax situation is definitely complex, but with proper planning and the right resources, it's totally manageable. Good luck with the move!

Quick tip from someone who's been an independent contractor for 7+ years: GET QUICKBOOKS SELF-EMPLOYED! It links to your bank accounts and credit cards, automatically categorizes expenses, tracks mileage with GPS, and separates business from personal stuff. Makes tax time so much easier! The mileage tracker alone saved me almost $3k in deductions last year because i literally just open the app when i start driving to a job site and it does everything automatically.

As someone who's been doing contract work for about 3 years now, I can definitely relate to the overwhelming feeling of trying to figure out all the deductions! A few things that really helped me: 1. **Set up a simple system NOW** - I wish I had started tracking everything from day one instead of trying to reconstruct expenses later. Even a basic spreadsheet with columns for date, amount, category, and description works wonders. 2. **Don't forget about business use of your home** - Even if you're on the road most of the time, if you do any administrative work from home (scheduling, invoicing, etc.), you might qualify for the simplified home office deduction. It's $5 per square foot up to 300 sq ft. 3. **Consider forming an LLC** - This won't help with this year's taxes, but for next year it can provide liability protection and potentially some additional tax benefits depending on your situation. 4. **Save for taxes religiously** - I learned this the hard way my first year. Set aside 25-30% of every payment you receive. Open a separate savings account just for taxes so you're not tempted to spend it. The learning curve is steep but once you get a system down, it becomes much more manageable. You're already ahead of the game by thinking about this stuff early in the year instead of scrambling at tax time!

Logan, you're absolutely right and your brother is wrong. As someone who's been self-employed for over 8 years, I can confirm that health insurance premiums do NOT reduce your self-employment tax liability. You'll pay the full 15.3% SE tax on your entire net profit from Schedule C, then get to deduct the health insurance premiums later on Form 1040 Schedule 1. This is one of the most common misconceptions about self-employment taxes. The health insurance deduction is what's called an "above-the-line" deduction that reduces your adjusted gross income for regular income tax purposes, but it happens after SE tax is calculated. So in your case with $750/month ($9,000/year) in premiums, you'll still pay SE tax on your full 1099 income, but you'll save on income tax by deducting those premiums. It's frustrating because it feels like it should be a business expense, but the IRS treats it as a personal deduction with special rules for self-employed folks. Show your brother IRS Publication 535 - it clearly states that health insurance premiums are not deductible as business expenses on Schedule C. You can find it on the IRS website. Good luck settling that family argument!

I'm dealing with this exact situation right now as a new freelancer! This thread has been incredibly helpful in clearing up the confusion. I was about to make the same mistake your brother suggested and deduct my health insurance premiums from my Schedule C profit before calculating SE tax. It's really counterintuitive that something so essential for running a business (staying healthy so you can work) isn't treated as a business expense. I'm paying about $650/month for my plan, so that's almost $8,000 a year that I'll be paying the full 15.3% SE tax on even though it's going straight to health insurance. One thing I'm curious about - does anyone know if there are any proposed changes to this rule? It seems like such an unfair burden on self-employed people compared to traditional employees who get pre-tax health benefits. We're already paying double the Social Security and Medicare taxes, and then we can't even get health insurance to reduce that base. Thanks to everyone who shared their experiences and the resources like the IRS publications. This is definitely one of those tax rules that catches a lot of new freelancers off guard!

Honestly the most straightforward way to handle this is to file your own taxes separately from your dad. You can tell him you want to learn financial independence without sharing the details. Use something like FreeTaxUSA which handles self-employment pretty well and is actually free (unlike some "free" services that charge for Schedule C). Just make sure to set aside about 25-30% of what you make for taxes since you'll owe both income tax and self-employment tax (15.3%) on your profits. First-time side hustlers often get shocked by that self-employment tax.

Just wanted to add that you should also consider what happens if your income grows beyond what you initially expect. I started selling handmade jewelry thinking I'd make maybe $1,000 a year, but ended up making $8,000 because demand was higher than expected. When you cross certain income thresholds, you might need to make quarterly estimated tax payments to avoid penalties. The IRS expects you to pay taxes as you earn, not just once a year. If you owe more than $1,000 in taxes when you file, they can hit you with underpayment penalties. Also, keep really good records from day one - screenshots of all payments, receipts for any business expenses, mileage if you drive anywhere for the business, etc. It's so much easier to track this stuff as you go rather than trying to reconstruct everything at tax time. A simple spreadsheet or even a notes app on your phone works fine when you're starting small.