Has anyone used TurboTax to file with Sweater Ventures investments? I'm wondering if it handles the forms correctly or if I should use a CPA this year since I started investing.

As someone who just went through my first year of investment taxes, I can totally understand your nervousness! Here's what I wish I had known starting out: First, don't let tax fear keep you from investing - it's really manageable once you understand the basics. Sweater Ventures should provide you with all necessary tax documents (likely K-1 forms as others mentioned) by mid-March typically. My biggest piece of advice: start a simple spreadsheet right now to track your investments. Note the date, amount invested, and any distributions received. Even though the platform will provide documents, having your own records helps you double-check everything. Also consider opening your first investments through a Roth IRA if you're eligible - the tax implications are much simpler since you've already paid taxes on the money going in, and qualified withdrawals in retirement are tax-free. Many platforms including Sweater allow IRA investments. The tax complexity really isn't as bad as it seems from the outside. Take the leap - you can always start small and learn as you go!

Have you tried reaching out to your local Taxpayer Advocate Service? They might be able to help if you're having trouble getting through to the IRS directly.

@Brady Clean mentioned the Taxpayer Advocate Service - that's actually a great suggestion! I used them last year when I was stuck in a similar situation. They're like a lifeline when the regular IRS channels aren't working. You can find them at taxpayeradvocate.irs.gov or call 1-877-777-4778. They're specifically designed to help when you're having problems getting through normal channels. Worth a shot before paying for third-party services!

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.

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.

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.

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.

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.

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.