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Don't forget about Required Minimum Distributions! Since you mentioned only withdrawing from Roth accounts now, I'm assuming you might have traditional IRAs or 401ks too? Once you hit 73, you HAVE to start taking RMDs from those accounts, which could push more of your Social Security into taxable territory in future years. Might be worth considering some Roth conversions now if you're in a lower tax bracket.
This is great advice. I did this exact thing - strategic Roth conversions for 3 years between retirement and when my RMDs kicked in. Saved a ton on lifetime taxes and now almost none of my SS is taxable.
StarStrider
Just a heads-up on PA taxes - while PA doesn't tax Social Security, they DO tax distributions from IRAs, 401ks and other retirement accounts (except military). Even if you paid PA tax on the money when you contributed, they tax it again when you withdraw. One of the few states that does this. Roth withdrawals are the exception since they're federally tax-free. So your strategy of using Roth money is smart from a PA perspective too!
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Justin Evans
Look, I'm just gonna say what everyone's thinking - these "miracle" tax preparers are committing fraud and getting their clients bigger refunds by lying on their tax returns. My sister went to one of these "magic" preparers three years ago and just got hit with a $11,000 bill for back taxes, penalties and interest after an audit. The preparer claimed a bunch of business expenses for a "side business" my sister didn't actually have, took deductions she wasn't eligible for, and even claimed her roommate as a dependent. The refund was amazing that year, but now she's on a payment plan with the IRS and it's a nightmare. The preparer? Nowhere to be found, of course.
Emily Parker
ā¢This is what scares me about these situations. Did your sister have any idea the preparer was doing shady stuff? Like did she sign the return without reviewing it, or did the preparer hide what they were doing?
Justin Evans
ā¢She had some suspicions when her refund was so much higher than usual, but the preparer assured her everything was "industry standard" and "completely legal tax strategies." My sister didn't understand all the tax jargon and forms, so she trusted the "professional." The preparer had her sign the final return without really explaining the details, and my sister didn't carefully review what was filed. The reality is that most people don't understand tax forms well enough to catch these issues, which is exactly what these shady preparers count on. When the audit came, the preparer's phone was disconnected and the office was empty.
Ezra Collins
Has anyone tried just asking this tax lady straight up how she gets such big refunds? I mean, there are legitimate tax strategies that many people miss. Before assuming fraud, maybe find out what she's actually doing?
I tried this approach with a similar situation. I asked the preparer to explain specifically what deductions she was claiming and why I qualified. She got super defensive and vague, saying things like "I have 20 years of experience" and "I know what I'm doing." When I insisted on seeing the actual forms before filing, she tried to rush me through signing. Huge red flag.
Ezra Collins
ā¢That definitely sounds suspicious! You're right that a legitimate tax professional should be able to clearly explain their strategy without getting defensive. I guess the best approach is to ask specific questions and expect specific answers. I still think there's a small chance this person just knows the tax code really well and finds legitimate deductions others miss, but the defensiveness you described would make me walk away too. Thanks for sharing your experience!
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Speaking as someone with background in corporate finance, there's another issue nobody's mentioned yet. Selling new stock isn't a tax-free event for the company the way you're describing. When a company issues new shares at above par value (which is typically pennies per share), the excess amount received is recorded as "additional paid-in capital," but it's not tax-free income. Companies don't pay income tax on true equity investments because those aren't considered revenue - they're capital contributions. But if the IRS determines you're artificially inflating the stock price to disguise what's basically product revenue, they'll reclassify it. Also, regular buybacks of stock from customers at below the issue price creates a whole host of securities problems around market manipulation. The SEC wouldn't look kindly on a system designed to issue overpriced shares with the expectation customers will take a loss selling them back.
Jay Lincoln
ā¢Would it make any difference if the company structured this as a membership program instead of actual stock? Like what if customers bought a "premium membership" that came with the product, and members could later sell back their membership at a reduced rate if they wanted to exit the program?
A membership program would face similar issues if it's just a disguised product sale. The IRS evaluates the economic reality of transactions. However, legitimate membership programs with actual ongoing benefits (beyond just getting one product) might be viewed differently. The key distinction is whether there's a genuine business purpose beyond tax avoidance. If members receive ongoing privileges, exclusive access, or other continuing benefits, and the pricing reflects fair market value for those benefits, then it starts looking more like a legitimate business model rather than a tax avoidance scheme.
I'm not a tax expert but I think everyone's missing the critical flaw here - who would actually buy stock at $195 that's publicly known to be worth $30? Even with a "free" product, customers would recognize they're effectively paying $165 for the product and taking on the hassle of owning and then selling stock. Most customers would simply prefer to pay directly for the product rather than jumping through these hoops, especially when they realize they're effectively paying the same amount either way. Plus, if you're publicly acknowledging the stock is worth $30 in your marketing materials (which you'd need to do for securities compliance), the whole scheme becomes transparent and pointless.
Exactly! And imagine the customer experience. "Congratulations on your purchase of our widget! Now please fill out these stock transfer forms, provide your social security number for securities reporting, and don't forget you'll need to report this capital loss on your Schedule D next tax season!" Nobody wants that hassle for a regular product purchase.
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Nick Kravitz
Tax strategy vs fraud also depends a lot on which software you use to file. Some tax programs actually warn you when something might cross the line or create audit risk. I use TurboTax and it flagged when I was getting too aggressive with home office deductions and explained why it might be considered fraudulent.
Hannah White
ā¢I've found FreeTaxUSA actually does a better job with these warnings than TurboTax. It explains the actual tax code reasons why something might be questionable rather than just giving generic warnings.
The distinction I've always used: Strategy is what you discuss openly with your tax preparer and would be willing to explain to an IRS agent. Fraud is what you hide or would be embarrassed to admit to during an audit. If you're worried about whether something crosses the line, that gut feeling is usually worth listening to. The tax code has plenty of legitimate ways to minimize taxes without venturing into shady territory.
Owen Devar
Just a heads up that you can get free tax help through the VITA program if your income is under $60k! They can help with filing previous years too. I volunteered there last year and we helped tons of people in similar situations with unfiled returns.
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Daniel Rivera
ā¢Where do you find these VITA locations? And do they have appointments or is it just walk-in? I've never filed and have W-2s going back to 2021 š¬
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Owen Devar
ā¢You can find VITA locations by using the IRS VITA Locator tool on their website or by calling 800-906-9887. Most locations operate by appointment, but some do accept walk-ins depending on volunteer availability. For your situation with multiple unfiled years, I'd definitely recommend making an appointment and specifically mentioning that you have returns for multiple years. Bring all your tax documents for 2021, 2022, and 2023 with you. They can help with all of them, but keep in mind they might need multiple sessions since each year is a separate return. The assistance is completely free as long as your income is within their guidelines!
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Sophie Footman
Has anyone here actually gotten hit with penalties for filing late? I'm in a similar situation (haven't filed 2023) but I'm pretty sure I OWED money so I'm scared to file now.
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Isla Fischer
ā¢Yes, unfortunately if you owed taxes, the penalties can add up quickly. There are two main penalties: the failure-to-file penalty (usually 5% of unpaid taxes per month, up to 25%) and the failure-to-pay penalty (usually 0.5% per month). Plus, interest accumulates on both the unpaid tax and penalties.
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Sophie Footman
ā¢Yikes that sounds bad. Is there any way to get those penalties reduced? I honestly just completely forgot to file, it wasn't intentional.
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