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Don't forget about the estate tax loophole! The wealthy use trusts and life insurance to pass MILLIONS to their kids tax-free while regular people get nothing. The stepped-up basis at death is another huge advantage - all the capital gains on investments essentially disappear when assets are inherited.
Stepped-up basis is actually available to everyone though, not just the wealthy. My dad left me some stocks he bought in the 90s, and I didn't have to pay any tax on all those years of gains when I sold them. I'm definitely not rich. Some of these strategies ARE available to regular folks, we just don't know about them.
The system really is designed with built-in advantages for different types of income and wealth levels. What frustrates me most is that many of these "loopholes" aren't actually loopholes - they're intentional policy decisions that favor capital over labor. For example, the carried interest provision that lets private equity managers pay capital gains rates (around 20%) instead of ordinary income rates (up to 37%) on what is essentially their salary. That's not available to regular employees no matter how good our accountants are. But there are some strategies middle-income folks can use that we often overlook: - Tax-loss harvesting in taxable investment accounts - Bunching itemized deductions in alternating years - Contributing to dependent care FSAs if you have kids - Taking advantage of the American Opportunity Tax Credit for education expenses The real barrier isn't just the cost of fancy accountants - it's that the most lucrative strategies require having significant assets or business ownership to begin with. You can't depreciate real estate you don't own, and you can't defer income you don't control the timing of. The system isn't broken by accident - it's working exactly as designed to reward wealth accumulation over wage earning.
This is exactly what I needed to hear - that it's not broken, it's working as intended. I've been beating myself up thinking I was just too dumb to figure out these strategies, but you're right that most of them require assets I don't have. I'm definitely going to look into tax-loss harvesting since I do have some investments in my taxable account. And the bunching deductions idea is interesting - can you explain how that works? Like alternating between standard deduction one year and itemizing the next? It's frustrating to realize the game is rigged from the start, but at least now I can focus on the strategies that are actually available to someone in my income bracket instead of chasing impossible dreams.
Does anyone know if using a PEO (Professional Employer Organization) for remote workers changes the nexus situation? My client is considering using a PEO to handle their multi-state employees to simplify compliance.
Using a PEO doesn't eliminate nexus concerns. The workers are still physically performing services in those states on behalf of your client's business, even if technically employed by the PEO. Most states look at the economic reality rather than the legal structure. PEOs can definitely help with payroll compliance across multiple states, but for income tax nexus, your client would still likely need to file in those states. The advantage is the PEO handles all the payroll tax registrations and filings, which is a big administrative relief.
This is such a helpful thread! I'm dealing with a similar situation with my consulting practice. One thing I learned the hard way is to also check if the states where your remote employees work have any specific registration requirements beyond just income tax filing. For example, some states require you to register as a "foreign entity" doing business in their state if you have employees there, even if you're just an LLC from another state. This can involve additional fees and annual reports that are separate from your tax filings. Also, don't forget about potential local taxes! Some cities and counties have their own business taxes or licensing requirements that might apply to businesses with employees working within their jurisdiction. It's not just about state-level compliance. I'd recommend creating a compliance calendar once you figure out all the filing requirements across the different states. Multi-state tax compliance can get overwhelming fast if you don't stay organized!
This is such a great point about foreign entity registration! I hadn't even considered that aspect when I was researching this for my client. It's already complicated enough figuring out the income tax nexus rules, and now there's a whole other layer of compliance to think about. Do you happen to know if there are any good resources that compile these foreign entity registration requirements by state? Or is it just a matter of checking each state's Secretary of State website individually? The compliance calendar idea is brilliant - I can already see how easy it would be to miss deadlines when you're dealing with multiple states that all have different requirements and due dates. Also, the local tax consideration is something I definitely need to look into. I know my client's Kentucky employee works from Louisville, so I should probably check if there are any city-level requirements there too. Thanks for sharing your experience - it's really helpful to hear from someone who's actually navigated this maze before!
Just want to add that timing matters here too. If you were married on ANY day in 2024, the IRS considers you married for the ENTIRE tax year when filing your 2024 taxes in 2025. So your marital status on December 31st determines your filing status for the whole year.
That's not entirely accurate. While that's the general rule for US citizens, there's a special "last day of the year" rule that applies when one spouse is a nonresident alien. The couple can choose to treat the nonresident spouse as a resident for tax purposes, but it's an election they make, not automatic.
I went through this exact same situation two years ago when I married my wife from the Philippines! Here's what I learned after making some mistakes the first time around: You definitely CAN file Married Filing Jointly even without your wife having an SSN - you'll need to get her an ITIN first. But here's the key thing that tripped me up initially: make sure you understand the "nonresident alien spouse election" that Marcus mentioned. You can elect to treat your nonresident spouse as a US resident for tax purposes, which opens up joint filing. One tip that saved me a lot of headaches: before applying for the ITIN, call the IRS (or use one of those callback services others mentioned) to confirm which specific documents they'll accept from your wife's country. Different countries have different acceptable documents, and the IRS agents can tell you exactly what works best. Also, don't stress too much about the foreign income reporting if you do file jointly - most countries have tax treaties with the US that prevent double taxation. My wife's income from the Philippines was covered by the Foreign Earned Income Exclusion, so it didn't actually increase our US tax burden. The whole process took about 3 months from start to finish, but it was definitely worth it for the tax savings compared to filing single. Good luck!
Has anyone formed an LLC in New Mexico? I've heard good things about their privacy laws and low fees, which seem important for expats.
I formed my LLC in New Mexico while living in Thailand. The privacy is good (similar to Wyoming), and annual fees are low ($0 annual report fee). The problem came with banking - many banks weren't familiar with New Mexico LLCs and their privacy features, which made opening accounts harder. I eventually switched to Wyoming because it had better name recognition with financial institutions. If banking isn't a concern though, New Mexico is solid.
As someone who went through this exact process two years ago while living in Portugal, I'd strongly recommend Wyoming for your situation. The combination of strong privacy protections, low annual fees ($60), and no state income tax makes it ideal for expats running online businesses. A few practical tips from my experience: 1. Don't worry about matching your driver's license state - choose based on business benefits, not past connections 2. Use Northwest Registered Agent or similar for your registered agent service - they're reliable and expat-friendly 3. For banking, I had success with Relay Financial and Mercury - both are online-first and work well with foreign addresses 4. Keep detailed records of your foreign residency (lease agreements, utility bills, etc.) as this will be important for tax purposes One thing to consider: since you're serving US clients, make sure you understand the tax implications. Even with a Wyoming LLC, you'll still need to file US federal taxes as a citizen, and depending on your income level, you might benefit from the Foreign Earned Income Exclusion. The key is getting everything set up properly from the start - it's much easier than trying to fix issues later when you're dealing with international time zones and communication barriers.
This is exactly the kind of detailed advice I was hoping for! Quick question about the Foreign Earned Income Exclusion - does that apply to LLC income or just W2/employment income? I'm planning to pay myself through the LLC but wasn't sure if consulting income through an LLC would qualify for the exclusion. Also, have you had any issues with Portuguese tax authorities regarding your US LLC income?
Great question about the FEIE! For single-member LLCs, the income is typically treated as self-employment income and reported on Schedule C, which can qualify for the Foreign Earned Income Exclusion as long as you meet either the physical presence test (330 days outside the US in a 12-month period) or the bona fide residence test. However, there's an important caveat - if your LLC income is considered "passive" rather than "earned" income, it might not qualify. Since you're doing consulting work, that should definitely count as earned income from your personal services. Regarding Portugal - yes, I do have to report my US LLC income to Portuguese tax authorities since I'm a tax resident here. Portugal has a tax treaty with the US that helps prevent double taxation, but I still need to file in both countries. The good news is that Portugal has the NHR (Non-Habitual Resident) program which can provide significant tax benefits for certain types of foreign income during your first 10 years of residency. I'd strongly recommend consulting with a tax professional who specializes in US-Portugal tax issues - the interaction between LLC taxation, FEIE, and Portuguese tax law can get complex quickly. The investment in proper tax advice upfront will save you headaches later.
Grant Vikers
I went through this exact situation with my daughter's ITIN. Here's what worked for me: 1. First, call the dedicated ITIN unit at 1-800-908-9982 2. Have your tax return info ready - they'll ask for the tax year and your information 3. Request a status check on the ITIN application 4. If they can't find it, ask if you should submit Form 4506-T to request verification 5. If no record exists, you'll need to reapply with a new W-7 6. When reapplying, consider using a Certified Acceptance Agent (CAA) who can verify your original documents 7. This prevents sending originals to the IRS The whole process took about 6 weeks once I reapplied properly.
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Diego Flores
I had a very similar experience with my nephew's ITIN application in 2022. What I learned from calling the ITIN hotline is that sometimes the applications get "suspended" in their system when there's a minor documentation issue, but they don't always notify you about it. In my case, the birth certificate copy I submitted wasn't clear enough, but instead of rejecting it outright, they just held the application in limbo. The agent was able to tell me exactly what was missing and I resubmitted just that document. Got the ITIN number about 8 weeks later. Definitely call 1-800-908-9982 first before doing anything else - they can see the status even if you never received any correspondence from them.
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