I don't think anyone's addressed your marriage plans for 2024. Remember that your filing status is determined by your status on December 31st of the tax year. So if you get married anytime in 2024, you'll be considered married for the entire 2024 tax year. If you're married filing jointly in 2024, you can't file as Head of Household, regardless of your parent situation. If you're married filing separately, you might qualify for HOH in very limited circumstances (like if you're considered "unmarried" because you lived apart from your spouse for the last 6 months of the year). For 2023 though, since you're still single, the dependent parent question is definitely worth figuring out!

Just wanted to add another perspective on this since I dealt with something very similar. My parents are also married and on Social Security only, and I was able to claim my mom as a dependent last year. The key thing that made it work was documenting exactly how much support I provided versus their total support needs. I kept detailed records of everything - mortgage payments I made for them, utilities, groceries, medical expenses, home repairs, etc. Then I calculated their total living expenses for the year and proved I paid more than 50%. For the gross income test, since Social Security was their only income and it wasn't taxable at their income level, my mom passed that test easily. The joint return test was satisfied because they didn't file any return at all. However, I couldn't qualify for Head of Household because they live in their own home, not with me. A parent can be a qualifying person for HOH even if they don't live with you, but only if you can claim them as a dependent AND you pay more than half the cost of maintaining their household as their main home. One thing to watch out for - make sure you have really solid documentation of all the support you're providing. The IRS can be pretty strict about this if they audit dependency claims.

I'm still confused about one thing - is the GSTT calculated on the amount AFTER the gift tax is paid or on the original amount? For example, if I'm giving $1M to my grandson and I've used up all exemptions: 1) Do I pay 40% gift tax ($400k) and then 40% GSTT on the remaining $600k ($240k) for a total of $640k tax? OR 2) Do I pay 40% gift tax ($400k) and 40% GSTT on the full $1M ($400k) for a total of $800k tax? The difference is huge!

This is such a helpful thread! I'm dealing with a similar situation where my elderly father wants to set up education funds for his great-grandchildren, and we were completely shocked when our attorney mentioned the potential for 80% combined taxation. One thing I learned from our estate planning attorney that might help others: if you're making direct payments for education or medical expenses, those payments don't count as taxable gifts at all - no gift tax AND no GSTT - as long as you pay the institution directly instead of giving the money to the family member. So instead of giving your grandchild $50,000 for college (which would trigger both taxes if exemptions are used up), you can pay $50,000 directly to the university with zero tax consequences. Same with medical bills - pay the hospital or doctor directly. It's not a complete solution for large wealth transfers, but it's at least one way to help the younger generations without getting hammered by taxes. We're now structuring my father's gifting strategy around maximizing these direct payments plus the annual exclusions before considering any larger transfers that would trigger the double taxation nightmare.

One major thing nobody's mentioned yet is sales tax nexus. Even without physical presence, many states now have economic nexus laws after the South Dakota v. Wayfair case. You'll likely need to collect and remit sales tax in states where you exceed certain thresholds (usually $100k in sales or 200 transactions). Given your international setup, you should really budget for a good sales tax compliance software from day one. TaxJar or Avalara aren't cheap but they're way cheaper than getting hit with penalties later. Delaware and Florida are pretty similar here - your sales tax obligations depend on where your customers are, not where you incorporate.

Great question! I went through this exact decision process for my SaaS startup last year as a non-US founder. Here's what I learned: **Delaware vs Florida for your situation:** Since you won't have physical presence in either state, you're looking at franchise taxes as the main difference. Delaware charges an annual franchise tax (minimum $175-400 depending on method), while Florida has no franchise tax but charges an annual report fee (~$139). **Entity choice recommendation:** For international e-commerce with growth plans, I'd strongly recommend Delaware C-corp. Here's why: - Clean separation between personal and business taxes (crucial for international founders) - Investor-ready if you ever want to scale - Well-established legal framework for disputes - Most US banks and payment processors are familiar with Delaware corps **Hidden taxes to watch:** - Sales tax nexus in customer states (this is huge - budget for compliance software early) - Customs duties and import taxes (varies by product classification) - Potential state income tax in states where you have employees later - GILTI tax on foreign-controlled US corporations (if you own >50%) **Banking tip:** Mercury and Brex both work well with Delaware corps and foreign founders. Start the banking process early - it takes longer for international owners. The state choice matters less than getting your sales tax and import duty strategy right from day one. Those will likely be your biggest ongoing tax obligations.

I completely understand your anxiety about this - the "jeopardy" language is definitely designed to get your attention! Here's what I'd recommend based on your situation: **Don't wait** - even though you're only waiting for one W2, that lien/levy notice means the IRS is ready to take action. A few key points: 1. **Call the IRS immediately** at the number on your notice. Explain you're waiting for a missing W2 and plan to file soon. They can often put a temporary hold (60-90 days) on collection actions. 2. **Request your wage transcript** from IRS.gov while you wait - this shows all reported W2 info and might have enough detail to file without the physical W2. 3. **Set up a minimal payment plan** if you can't reach them by phone. Even $25/month stops collection and shows good faith. Online setup is only $31 vs $107 by phone. The key thing is **communication** - the IRS doesn't know you plan to pay with your refund. From their perspective, you're just ignoring a debt. Once you make contact and explain your situation, they're usually reasonable about working with you. Don't risk a lien on your credit report over $650 - it's not worth the long-term damage for a relatively small amount. Take action today!

I had almost this exact same situation last year - owed about $700 and got that scary "jeopardy" notice while waiting for a delayed 1099 from a freelance gig. The language in those notices is definitely designed to get you moving fast! Here's what worked for me: I called the IRS number on the notice (took about 2 hours on hold, but I got through). The agent was actually really understanding when I explained I was just waiting for tax documents. She put a 90-day collection hold on my account, which gave me plenty of time to get everything sorted out. The key thing they told me is that once you receive that "lien/levy warning," you're basically at the final stage before they take action. They don't know you're planning to use your refund to pay it off - from their system, it just looks like you're ignoring the debt. Don't stress too much about the $650 amount, but definitely don't ignore the timeline. Even setting up a $25/month payment plan online would stop the collection process immediately if you can't get through by phone. You can always pay it off in full once you file and get your refund. The worst thing you can do is nothing - I've seen people end up with liens over tiny amounts just because they thought it wasn't worth dealing with. Take care of it this week!

I went through this exact situation when I married my husband who had tax debt from 2019-2020. The key thing to understand is that you won't become personally liable for her pre-marriage debt, but the IRS absolutely can and will take your joint refund to pay it off. Here's what I learned: First, definitely file Form 8379 with your joint return if you're expecting a refund. This protects your portion based on your income, withholding, and credits. Second, consider doing a "tax projection" calculation - sometimes the tax savings from filing jointly are so significant that even losing part of your refund to her debt, you still come out ahead compared to filing separately. One thing that caught me off guard was that the IRS applied our entire refund to my husband's debt initially, even though I had filed Form 8379. It took about 4 months to get my portion back. So if you need that money quickly, plan accordingly. Also, make sure your wife is current on any payment plans for her debt - if she's in default, it can complicate things further. The innocent spouse provisions protect you from liability, but they don't protect your refund from offset. Those are two different things that people often confuse. Good luck!

This is such a common worry for newlyweds! I went through the same anxiety when my spouse disclosed their tax debt after we got engaged. The short answer is no - you won't become liable for tax debt that existed before your marriage. However, the IRS can still grab your joint refund to pay toward that debt. Here's my advice based on what worked for us: Calculate whether filing jointly still saves you money even after losing part of your refund. In many cases, the tax savings from joint filing exceed what you'd lose to the debt offset. Also, start planning now - if you know you'll lose part of your refund, consider adjusting your withholdings so you're not giving the IRS an interest-free loan all year. One more tip: Get copies of all the notices your wife received about her tax debt. Understanding exactly how much she owes and whether she's on a payment plan can help you make better decisions about filing status and refund expectations. The IRS is actually pretty reasonable to work with once you understand the rules - it's the uncertainty that's stressful!