Does anyone know if forming the holding company in a different state than where you live would make sense from a tax perspective? I've heard Wyoming and Nevada mentioned a lot for holding companies because they have no state income tax.

I went through a similar situation about 18 months ago with roughly the same income level as you. Here's what I learned that might help: First, don't get too caught up in the complexity right away. With $150K in business income plus rental properties, you're definitely at a level where this could make sense, but the structure needs to match your specific goals. One thing I wish someone had told me earlier: the "tax savings" from holding companies often come more from better expense management and strategic timing rather than just the entity structure itself. For example, being able to reimburse yourself for health insurance, home office expenses, and business travel through the holding company can add up to significant deductions. For your rental properties specifically, having them in separate LLCs under a holding company does create nice liability separation, but make sure you understand the ongoing costs. Each LLC typically needs its own tax return (even if it's a simple one), and depending on your state, there might be annual fees for each entity. My accountant had me run the numbers on three scenarios: staying as sole proprietor, setting up just the business as an S-Corp, and doing the full holding company structure. The holding company only made sense once we factored in my plans to acquire more properties over the next few years. The income flow question you asked is key - with an S-Corp holding company, everything flows through to your personal return, so you're not dealing with corporate-level taxation plus personal taxation. Much cleaner than I initially expected.

PSA: Make sure your Cash App is verified/activated for direct deposit before the refund hits! Learned that one the hard way last year smh

Been using Cash App for my refunds for 3 years now. From my experience, it's usually 1-2 days early but not always the full 2 days they advertise. Last year I got mine on a Wednesday when my DDD was Friday. The year before it was just 1 day early. Honestly depends on when the IRS actually processes your batch and sends it out. Don't stress too much about the exact timing - you'll get it soon either way!

Great to see you taking a proactive approach with this situation! One additional thing to consider - if your employer does classify you as a contractor but you believe you should be an employee, you can file Form SS-8 with the IRS to request an official determination of your worker status. This form asks detailed questions about your work relationship and the IRS will make a binding determination. It takes several months to get a response, but it gives you official documentation if there's ever a dispute. You can also file Form 8919 when you file your taxes to pay only the employee portion of Social Security and Medicare taxes if you believe you were misclassified. Just be aware that filing these forms essentially reports your employer to the IRS, so it could strain your working relationship. Most people try to resolve it directly with the employer first, but it's good to know these options exist as a backup plan. Also, document everything from your conversations with your boss about this arrangement. If the IRS ever investigates, having written records of how the classification decision was made can be very helpful for your case.

This is such a common situation and I'm glad you're getting good advice here! I went through something similar with a tech startup about two years ago. They kept pushing the "flexibility" angle of contractor status, but what they really wanted was to avoid paying their share of employment taxes. Here's what I learned the hard way: even if you negotiate a higher rate to offset the self-employment taxes, you're still losing out on other employee protections. No unemployment insurance eligibility, no workers' comp coverage, and in many states you lose certain labor law protections. The "business expense deduction" argument they're making is often oversold too. Unless you're actually incurring significant expenses that are directly related to the work (separate from your side business), those deductions won't be as valuable as they make it sound. I'd strongly recommend pushing for proper W-2 classification. If they're a legitimate business, setting up payroll isn't actually that complicated - there are plenty of services like Gusto or ADP that make it pretty straightforward for small companies. The fact that they're calling it a "hassle" makes me think they're more interested in saving money than doing right by their employees. Trust your instincts on this one - if it feels sketchy, it probably is.

For partnership taxation, the format matters less than consistent practice with examples. Whatever resource you choose, make sure to work through all the examples. I learned best by creating my own "case studies" and tracking basis through multiple years of contributions, operations, and distributions. One approach I found helpful was to start with a simple partnership with two equal partners, then work my way up to more complex scenarios - adding debt, special allocations, etc. Seeing how each new element affects the calculations helped me build a mental framework.

As someone who's been working with partnership taxation for about 15 years, I'd echo the book recommendations already mentioned - especially "The Logic of Subchapter K" as a starting point. But I wanted to add that the IRS's own "Advanced Issues in Partnership Taxation" course materials are actually quite good once you have the fundamentals down. They're available through the IRS website under their continuing education section. One thing I wish someone had told me early on: don't try to memorize all the rules at once. Partnership taxation is incredibly complex, and even experienced practitioners regularly reference materials. Focus on understanding the conceptual framework first - why partnerships are treated as pass-through entities, how basis protects partners from double taxation, and how allocations work in theory. The mechanical calculations become much easier once you grasp these underlying concepts. Also, consider joining the ABA Tax Section or your state's tax section - they often have partnership tax committees that publish practical guides and host webinars specifically for practitioners dealing with these issues.

Has anyone successfully amended a return after the 3-year mark specifically for EIC issues? Did you face penalties?

I went through almost the exact same situation last year with my 2017 return. The key thing to understand is that the IRS has sophisticated matching systems that will absolutely catch the conflict when your ex files their return claiming the same child. Here's what I learned: You're correct that the 3-year deadline is mainly for getting refunds back, not for correcting errors. The IRS can assess additional tax on EIC issues for up to 6 years, and in some cases longer. I'd strongly recommend filing that 2018 amendment even though you won't get a refund. When I did mine, I included a detailed explanation letter with my divorce decree attached, clearly stating which credits I was entitled to versus which ones I wasn't. The IRS processed it without issues and actually sent me a letter acknowledging my voluntary compliance. The fact that your ex never filed their 2018 return actually works in your favor - it shows the IRS that you were the one trying to comply with tax obligations while they were ignoring theirs. When they finally do file, your proactive amendment will be on record showing good faith. One tip: keep detailed records of everything related to your child's custody and living arrangements for 2018. If the IRS does audit, they'll want proof of who was actually entitled to what.