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Ethan Clark

Why can't middle/lower classes use the same tax loopholes as the wealthy? What makes these tax advantages so restricted?

I've been doing my taxes for years and I always see articles about how billionaires and corporations pay almost nothing in taxes while I'm getting hammered with 25% of my paycheck gone. What's stopping regular people like me from using the same tax strategies that rich people use? Is it just that we can't afford those fancy accountants and tax lawyers who know all the tricks? Or is there something more fundamental about these loopholes that makes them inaccessible to people earning normal salaries? I've heard about things like carried interest, depreciation on real estate, and offshore accounts, but whenever I try to research these things, it seems like you need to already be wealthy to benefit from them. I'm just trying to understand if there's any way for someone making $65k a year to use any of these strategies or if the system is just fundamentally designed to only work for the wealthy.

The tax code actually creates different opportunities based on income sources rather than income amounts. The wealthy typically have investment income (capital gains, dividends, business ownership) while middle-class folks mostly have wage income. The biggest "loophole" is simply that investment income is taxed at lower rates than wages. Long-term capital gains are taxed at 0%, 15%, or 20% depending on income level, while wages face rates up to 37% plus payroll taxes. This difference isn't about hiring fancy accountants - it's baked into the tax code itself. Another major difference is business ownership. When you own a business, you can deduct legitimate business expenses before calculating taxable income. Employees can't deduct most work-related expenses. The wealthy also benefit from timing control - they can choose when to sell investments to optimize their tax situation. While anyone can use some strategies (contributing to retirement accounts like 401(k)s and IRAs), the reality is that many advanced strategies require significant capital to implement effectively.

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So you're saying I need to own a business to get tax advantages? Can I just start a small side hustle and write off a bunch of my regular expenses as "business expenses" then? Like my car, home office, phone, etc?

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Starting a legitimate business can provide tax benefits, but it's not as simple as just writing off personal expenses. The business must have a genuine profit motive and the expenses must be ordinary and necessary for that business. The IRS looks closely at businesses that consistently report losses. For things like a home office deduction, you need to use that space exclusively for business purposes. Vehicle expenses can be deducted only for the business portion of use, which requires detailed mileage logs. Phone costs can be deducted based on the percentage used for business. The key is documentation and having a genuine business purpose - it's not just a way to write off personal expenses.

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I struggled with this same question last year after getting hit with a huge tax bill despite making way less than my boss. I found this AI tool called taxr.ai that actually analyzes your specific situation and explains exactly which tax strategies would benefit you most based on your income level and sources. It helped me understand why some deductions weren't available to me but showed me several I was missing. The site https://taxr.ai has this feature where it reviews your previous returns to find missed opportunities - found about $2,700 I'd overpaid last year because I didn't know about some deductions that were totally legal for my situation. It's like having one of those fancy accountants but without the crazy fees.

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Does it actually work for people with just regular W2 jobs? Or do you need to have investments and stuff? I'm skeptical because most tax software I've tried asks the same basic questions and gives me the same basic refund.

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Sounds like an ad tbh. How does it actually find deductions that TurboTax and other programs miss? I've tried a few different services and they all give me pretty much the same result.

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It absolutely works for regular W2 employees - that's exactly what I am. The difference is it found itemized deductions I didn't know I qualified for based on my state's specific rules. Most standard tax software focuses on federal returns and doesn't optimize for state-specific opportunities. It's different from basic tax software because it actually reviews documentation rather than just asking yes/no questions. For example, it identified that my student loan interest was partially deductible even though I was slightly over the income limit because of how my retirement contributions affected my AGI. No other program connected those dots for me.

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I was super skeptical about taxr.ai when I first saw it mentioned here (still thought it might be some kind of scam), but I was desperate after getting denied for several deductions last year. Figured I'd try it since they have that free analysis option. Honestly blown away by what it found. Turns out I could deduct a portion of my home internet and cell phone as a remote worker even though I'm a W2 employee, not a contractor. My regular tax guy never mentioned this! The software also identified a state tax credit for renters in my area that I had no idea existed. Just filed an amendment for last year and expecting about $1,400 back. Not rich people savings but definitely worth the time.

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The real problem isn't just knowing about tax strategies - it's getting through to the IRS when you have questions or problems. I spent MONTHS trying to call them to get clarity on some deductions I thought I qualified for, but could never get through. I finally used https://claimyr.com which got me connected to an actual IRS agent in about 15 minutes after I'd wasted weeks trying on my own. The agent confirmed I could use a particular education credit even with my income level. You can see how it works at https://youtu.be/_kiP6q8DX5c - basically jumps the phone queue for you. Made a huge difference in my return because I was able to correctly claim a credit my tax software said I didn't qualify for.

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Wait how does this even work? The IRS phone system is notoriously backed up. How can a third party service possibly get you through faster? Sounds like they're claiming to do the impossible.

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Yeah right. There's no way this works. The IRS phone system is completely broken, and I refuse to believe some random service can magically get you through when millions of people can't get answers. Probably just takes your money and puts you in the same queue everyone else is in.

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It works by using automated technology to continuously dial the IRS until a line opens up, then it calls you to connect. It's basically doing the redial work that would take you hours or days, but doing it automatically. There's no special "back door" - it's just efficiently working within the existing system. The difference is most people give up after a few tries or can't sit around hitting redial all day. This service does that part for you, and you only get charged if you actually get connected. I was skeptical too but when I needed answers about my education credits it was literally the only way I could get through.

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I need to eat my words. After posting that skeptical comment, I was still desperate about my tax situation (IRS sent me a notice saying I owed $4,200 I definitely didn't have), so I tried Claimyr even though I was 100% sure it wouldn't work. Got connected to an IRS agent in 23 minutes. TWENTY-THREE MINUTES. After trying for WEEKS on my own. The agent reviewed my situation and confirmed that the notice was actually an error on their end due to a mismatched form. They're sending a correction letter and I don't owe anything. This literally saved me thousands and hours of stress. Never been so happy to be wrong about something.

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Here's the real truth: The tax code favors wealth-building activities over earning wages. The main advantages wealthy people have: 1) They have money to invest, which gets preferential tax treatment 2) They have business entities that allow income flexibility and expense deductions 3) They can afford to tie up money in tax-advantaged investments long-term 4) They can donate appreciated assets to charity (avoiding capital gains taxes) The average worker CAN use some strategies though: - Max out retirement accounts (401k, IRA) - Use HSAs if eligible (triple tax advantage) - Take advantage of tax-loss harvesting with investments - Time major purchases/sales around tax years - Keep excellent records for any deductions you qualify for

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Are there any income-based phaseouts for retirement accounts though? I thought I read somewhere that high earners can't contribute to Roth IRAs?

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You're right about the Roth IRA income limits - for 2025, the contribution starts phasing out at $153,000 for single filers and $240,000 for married filing jointly. However, there's a completely legal workaround called a "backdoor Roth IRA" where high earners can make non-deductible traditional IRA contributions and then convert them to Roth. For 401(k)s, anyone can contribute regardless of income level, though the total amount is capped ($23,000 for 2025, plus an additional $7,500 if you're over 50). The truly wealthy use additional strategies like cash balance plans that allow much higher retirement contributions, sometimes over $300,000 annually for business owners nearing retirement.

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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.

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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.

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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.

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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.

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