Don't forget about state taxes! I sold some collectible comic books last year and was shocked that my state wanted a piece too. Depending on where you live, you might owe state income tax on the gains. Some states also have weird exceptions or special rates for collectibles.

One thing I haven't seen mentioned yet is timing considerations. If you're planning to sell multiple pieces, you might want to spread the sales across different tax years to manage your tax bracket, especially since collectibles are taxed at that higher 28% rate. Also, if any of the pieces have appreciated significantly since you inherited them, consider getting a current appraisal before selling. This can help establish fair market value for insurance purposes during the selling process, and it gives you documentation to support your sale price if the IRS ever questions it. For the $3,800-4,500 piece you mentioned, definitely keep detailed records of comparable sales you find online - screenshot them with dates. This kind of documentation can be really valuable if you need to justify your basis calculation later.

Honestly, instead of trying to opt out of Social Security (which is nearly impossible), you might want to focus on maximizing your retirement accounts like 401k, IRA, HSA etc. These give you tax advantages now while letting you control your own investments. The tax benefits can offset some of what you're paying into Social Security.

I understand your frustration with Social Security taxes - I felt the same way when I was starting my career. After researching this extensively, I can confirm what others have said: legitimate opt-outs are extremely limited and strictly regulated. The reality is that Social Security isn't just a retirement program - it also provides disability and survivor benefits that protect you and your family right now. Even if you're skeptical about future solvency, the program has never missed a payment in its 90-year history, and even worst-case projections show reduced benefits, not zero benefits. Rather than focusing on opting out (which likely isn't possible for your situation), consider this approach: maximize your tax-advantaged accounts first. If you're not already maxing out your 401(k), IRA, and HSA (if eligible), you're missing out on immediate tax savings that could be much more significant than your Social Security contributions. These accounts give you the investment control you're looking for while providing real tax benefits today. The 6.2% you pay into Social Security also comes with an employer match of 6.2%, so you're actually getting more value than it appears on your paycheck stub.

You're absolutely right to be excited about discovering QBI - it can make a real difference! Since you mentioned being comfortable with tax forms, I'd suggest starting with the 2021-2023 amendments yourself first. The QBI calculation is straightforward at your income level, and Form 8995 really does walk you through it step by step. One thing to double-check: if you were filing as a partnership with K-1s during some of those years, make sure you understand how QBI flows through on those returns versus your sole proprietor years. The deduction might be calculated differently depending on your filing structure for each year. Also, consider batching your amendments strategically. File one year first to get familiar with the process, then do the others. This way if the IRS has any questions about your first amendment, you can apply those lessons to the remaining years. And definitely keep detailed records of everything you send - make copies and use certified mail if filing paper returns. The potential refunds plus interest could really help with your financial situation, so it's worth the effort to get these filed properly!

One thing I haven't seen mentioned yet is that you should double-check whether your business activities actually qualify for QBI. The deduction applies to qualified trade or business income, but there are some exceptions. Most sole proprietorship activities qualify, but things like performing services as an employee or certain investment activities might not. Also, since you mentioned your income has been around $17,500 annually, you're well below the taxable income thresholds where QBI gets limited by W-2 wages or basis of property, so the calculation should indeed be straightforward - just 20% of your qualified business income. For the partnership years, the QBI would have flowed through to your personal return via the K-1, so you'd still claim it on your individual 1040 using Form 8995. The partnership itself doesn't claim the QBI deduction. Given the amounts involved and your comfort level with taxes, I'd definitely try doing the amendments yourself first. At your income level, you're looking at roughly $3,500 per year in QBI deductions (20% of $17,500), which could mean significant refunds especially if you were in the 12% or 22% tax brackets. That's potentially over $1,000 in refunds for the three years you can still amend, plus interest!

The discussion about regulatory specialization is spot-on, but there's another dimension worth considering: the Cayman Islands has also become a critical piece of international tax treaty networks. Many countries have tax treaties with the UK that extend to British Overseas Territories, giving Cayman-domiciled entities access to reduced withholding taxes and other treaty benefits that wouldn't be available in standalone tax havens. This treaty access is particularly valuable for institutional investors who need to efficiently move capital across multiple jurisdictions. A pension fund or sovereign wealth fund structuring investments through the Caymans can often access treaty benefits that reduce friction costs significantly compared to direct investment or using non-treaty jurisdictions. The irony is that this system was probably never intended to work this way - these treaties were designed for legitimate bilateral trade and investment between the UK and other countries, not to facilitate global fund structures. But the Caymans has effectively leveraged this historical accident into a sustainable competitive advantage that's much harder to replicate than simple tax rates. Even if there were perfect international coordination on corporate tax rates, the treaty network effects and regulatory specialization discussed earlier would likely keep the Caymans competitive. They've essentially built multiple layers of competitive advantage that work together synergistically.

This has been an incredibly enlightening discussion that really changed my understanding of how the Cayman Islands operates. When I first asked the question, I was thinking about it purely from a tax revenue perspective - why leave money on the table when you have all these companies registered there? But reading through all these responses, I realize I was completely missing the sophisticated economic model they've actually built. The combination of fee-based revenue, regulatory specialization, treaty network advantages, and network effects creates a much more sustainable and defensible position than simple tax competition ever could. The point about them essentially becoming the global infrastructure for alternative investments is particularly striking. They're not just offering low taxes - they're providing specialized legal and regulatory products that have genuine economic value and would be costly to replicate elsewhere. What's most impressive is how they've managed to evolve and adapt to international pressure while actually strengthening their competitive position. Instead of being undermined by transparency requirements, they've used compliance as a way to legitimize their role and differentiate themselves from less sophisticated tax havens. I guess the real answer to my original question is that they don't need to raise taxes because they've found a much smarter way to capture value from the global financial system while providing genuine services that their clients are willing to pay premium fees for. It's actually a pretty brilliant economic strategy when you look at it holistically.

Has anyone made this transition without going back to entry level positions? I've been in industry accounting for 8 years with no public experience, but have my CPA and am interested in moving to tax. Wondering if I should expect a pay cut or lateral move?

Your audit background from KPMG plus 6 years of staff accounting experience actually puts you in a great position for tax roles! Many firms value that combination because you understand both sides of financial reporting. I'd recommend starting with mid-tier firms like Grant Thornton, BDO, or regional players rather than jumping straight back to Big 4 tax. They're often more willing to train someone with your background and won't lowball you as much on level/compensation. For job titles, search for "Tax Associate," "Corporate Tax Analyst," or "Tax Consultant" - avoid anything with "Junior" or "Entry Level" since you have significant accounting experience. Your REG pass is huge - that's the hardest tax exam and shows you can handle complex tax concepts. One tip: When interviewing, emphasize how your audit experience helps you understand the financial statement impact of tax decisions. That's exactly what corporate tax departments need - someone who can see the bigger picture beyond just compliance. Your KPMG experience also shows you can handle demanding deadlines and complex clients, which translates directly to tax work. Don't sell yourself short - you're not starting from zero, you're pivoting with valuable transferable skills!