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Don't overlook checking if your original tax return was actually correct. I thought I owed $12k in back taxes until I had a tax professional review my return. Turns out I had missed several deductions as a self-employed person. Filed an amended return and my liability dropped to around $7,500. Worth spending a few hundred bucks on a CPA review if you did your taxes yourself originally. Even if you used software, it's only as good as the info you put in.
What kind of deductions did you miss? I'm self-employed too and worried I might be overpaying.
The biggest ones I missed were home office deductions (I was afraid of an audit so I skipped it entirely), health insurance premiums (which are deductible for self-employed people), and retirement plan contributions. I also hadn't properly calculated my business mileage. The CPA also helped me properly categorize some expenses I had lumped together as "miscellaneous" which gave me more legitimate deductions. Even things like a portion of cell phone bills and internet costs can be deductible if you use them for business.
Has anyone considered bankruptcy as an option for tax debt? I've heard that older tax debts can sometimes be discharged.
Yes, but there are very specific rules. Tax debts can potentially be discharged in Chapter 7 bankruptcy if they meet ALL these conditions: - The taxes are income taxes (not payroll or fraud penalties) - The debt is at least 3 years old (from the due date) - You filed your tax return at least 2 years before filing bankruptcy - The IRS assessed the tax at least 240 days before filing bankruptcy - You didn't commit fraud or willful evasion For 2022 taxes, you wouldn't meet the 3-year rule yet, so bankruptcy wouldn't help with this specific debt until at least 2026. Also, bankruptcy has serious long-term consequences for your credit and financial future.
One thing nobody's mentioned yet - check with your state tax authority too! Federal Section 121 exclusion is one thing, but some states have different rules or interpretations about primary residence. In my case (WA state), I had to provide additional documentation to prove my home was still my primary residence despite being gone for 16 months. I needed copies of my voter registration, utility bills (even though they were minimal since I wasn't there), and property tax statements. The county tax assessor had initially questioned my homestead exemption because a neighbor reported my house was "abandoned" when I was traveling. What a nightmare that was to clear up!
Thanks for bringing this up! I'm in Arizona - do you know if there are any specific state rules I should look into? I've maintained all my utilities and have been paying someone to check on the house monthly and do basic maintenance.
Arizona is actually pretty reasonable with their rules from what I know. The key is that you've maintained the utilities and have someone checking on the place - that shows intention to return and ongoing maintenance of the property as a residence. Check with the Arizona Department of Revenue to be sure, but they generally follow federal guidelines for primary residence. The fact that you've been paying for maintenance is a strong indicator that you haven't abandoned the property. Just make sure you have documentation of those payments for the maintenance person as additional proof if needed.
Has anyone actually been audited on this specific issue? I'm wondering because I'm in almost the exact same situation (traveling since 2021, selling house in 2025) and I'm curious what documentation the IRS actually requested.
I went through an audit in 2022 for my 2020 taxes that included questions about my primary residence status. They asked for: - Voter registration - Driver's license - Where my vehicles were registered - Bank statements showing my address - Tax returns from previous years - Utility bills - Homeowners insurance They never asked for proof I physically occupied the house for X days. It was all about where my legal ties were established.
One solution that worked for our family farm was negotiating a "guaranteed payment" instead of relying solely on distributions. A guaranteed payment is like a salary that gets paid regardless of profitability, and while it's still taxable, at least you actually RECEIVE the money to pay those taxes. Talk to the managing partners about amending the operating agreement to include this provision. We did this after three cousins nearly had to sell their shares because they couldn't afford the tax burden.
How exactly do you bring this up without causing family drama? My father-in-law gets defensive whenever I mention anything about the business structure or distributions.
The key is framing it as a business sustainability issue rather than a personal complaint. I approached it by saying: "For the business to thrive long-term, all owners need to be able to maintain their ownership without financial hardship." I also found it helpful to bring some documentation from our accountant explaining how other family businesses handle this common issue. When presented as a standard business practice rather than a criticism, it was received much better. Sometimes having a neutral third party (like an accountant) suggest these changes can remove the emotional element from the discussion.
Have you looked into whether you qualify for any deductions related to the business that might offset some of that tax burden? Since you're technically a business owner through those shares, you might be able to deduct certain expenses.
This is good advice. When I was in a similar situation, I was able to deduct a portion of my home office, travel to business meetings, and some professional development costs. It didn't solve the whole problem, but it reduced the tax hit by about 30%.
I hadn't even thought about deductions! I work from home occasionally on stuff related to the orchard (mostly bookkeeping and some marketing). Would that count toward a home office deduction? And we drive about 80 miles round trip to visit the orchard like 6-7 times a year.
You might want to request a hold on collections while they review your case. When I had a similar situation, I sent in Form 911 (Taxpayer Advocate Service request) and they put a temporary hold on collections while sorting everything out. The double counting of W-2s is actually a pretty common issue in their automated matching system.
Does requesting a hold on collections affect your credit score or create any other problems? I'm dealing with something similar but worried about making things worse.
Requesting a hold doesn't affect your credit score at all. The IRS doesn't report to credit agencies unless they've actually filed a tax lien, which wouldn't happen at this early stage in the process. The Taxpayer Advocate Service is actually designed specifically to help in situations like this where there's a clear error or hardship. Many people don't realize it exists, but they can be incredibly helpful when dealing with issues that aren't getting resolved through normal channels.
Make sure u keep EVERYTHING. All paperwork, copies of letters, proof of mailing (use certified mail!), and notes from any phone calls including agent ID numbers. IRS lost my response twice before and tried to say I never responded. The burden of proof is on you unfortunately.
Nina Fitzgerald
19 Another option that hasn't been mentioned is adjusting your state withholding separately. In many states, you can fill out a state-specific withholding form that's different from your federal W-4. I found out last year that even though I had my federal withholding dialed in perfectly, I was still having way too much withheld for state taxes. Check your state's tax department website - they usually have forms and calculators specifically for state withholding.
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Nina Fitzgerald
β’14 Oh I didn't realize state withholding was separate! Does changing your federal W-4 automatically adjust your state withholding too, or do you have to do both separately?
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Nina Fitzgerald
β’19 It depends on your state. In some states, your state withholding is based on your federal W-4, so changing one affects the other. But many states have their own withholding forms. For example, states like California (DE 4), New York (IT-2104), and Illinois (IL-W-4) have their own forms. Your employer's HR department should know which forms apply to your state. If you only adjust your federal withholding, you might still get a large state refund, so it's worth looking into both!
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Nina Fitzgerald
12 Careful about adjusting too much! My brother tried to get his refund to zero and ended up OWING $800 at tax time, which he wasn't prepared for. Maybe aim for a small refund of a few hundred as a cushion in case your tax situation changes during the year.
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Nina Fitzgerald
β’5 This is really good advice. I always aim to get a small refund (around $500) rather than break even exactly. Life changes happen - you might get a raise, have a side gig, or have investment income you didn't expect. That small cushion helps prevent a surprise tax bill.
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