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Just a heads up - when you're married filing separately, there are a bunch of other limitations beyond just the mortgage interest deduction. You lose a lot of credits and deductions when you choose MFS status. Have you considered whether filing jointly might be better overall, even with this mortgage interest situation?
We're definitely not in a position to file jointly given our separation, and I think we're past the point where we could amend to file jointly anyway. She's already filed her return claiming the full mortgage interest deduction, so I'm just trying to figure out if I can amend mine to get my fair share of it. But thanks for pointing that out!
When I went through my divorce, I learned you can actually request your ex's tax transcripts from the IRS if you filed a joint return in any previous years. Might be helpful to see exactly what she claimed so you know what you're dealing with.
As an additional tip - one thing that helped me immensely was creating a "tax events" document throughout the year. Every time something happens that might affect your taxes (starting a new client, buying business equipment, making charitable donations, etc.), I add it to a running document with the date and any relevant details. When tax time comes around, I'm not trying to remember everything that happened 9-12 months ago. Has saved me from missing deductions multiple times!
This is brilliant! Do you use any specific app or format to track these "tax events" throughout the year? I always find myself scrambling in April trying to remember everything that happened the previous year.
I keep it super simple - just a Google Doc that I can access from my phone or computer anytime. I have it organized by month, and I set a monthly calendar reminder to update it. For format, I just do bullet points with the date, what happened, and approximate dollar amount if applicable. For example: "3/12 - Bought new laptop for business use - $1,450" or "7/23 - Started contract work for ABC Company, expecting approximately $20k income through end of year." Nothing fancy, but it's saved me thousands in deductions I might have forgotten about!
Just want to add that most CPAs actually prefer clients who come organized rather than just dumping a shoebox of receipts on their desk. But don't go overboard creating elaborate spreadsheets that might actually make things harder. Ask your new accountant what format they prefer to receive information in. Some want digital files organized in specific ways, others have their own systems and prefer you just organize by category. A 15-minute phone call asking about their preferences could save both of you hours of frustration later.
That's a really good point. I didn't even think to ask my new accountant about their preferred format. I'll definitely reach out before I spend hours organizing everything in a way that might not be helpful to them.
As a practical matter, here's the breakdown of what you actually need: For a complex case like yours with $850k revenue, multiple unfiled years, and state levies already happening, you ideally want BOTH a CPA and a tax attorney, but in a way that minimizes cost. Here's what I'd recommend: 1. Have a CPA prepare all your actual returns with proper expenses (much cheaper than an attorney doing this) 2. Have a consultation with a tax attorney (1-2 hours) to assess if there's risk of criminal charges 3. If no criminal risk, let the CPA handle the IRS negotiations 4. If there is risk, then yes, retain the attorney I've gone through this with my business. Initially used just a CPA, but when the IRS started making noises about willful neglect, I brought in an attorney. The attorney only handled the specific negotiations and communications, while the CPA did all the preparation work. This hybrid approach kept my costs reasonable while still getting proper protection.
Would the original poster need to file business returns separately from personal returns? And what about sales tax - is that a completely different process? I'm confused about how all these different tax types get resolved.
Based on the description, it sounds like the business was likely a sole proprietorship or single-member LLC, which means business income would be reported on Schedule C of the personal return. So the CPA would prepare personal returns (Form 1040) with business schedules attached for each year. Sales tax is indeed a separate process handled at the state level. The CPA would need to prepare and file sales tax returns for all unfiled periods. This is separate from income tax filings but should be addressed simultaneously since the state has already started collection actions. Most tax resolution CPAs can handle both income and sales tax matters, but it's worth confirming this specifically when hiring someone.
Don't overlook the penalties here - they're gonna be massive after 5 years of non-filing. Make sure whoever you hire talks about penalty abatement. The IRS has "first-time penalty abatement" and "reasonable cause" options that could save you tens of thousands. I had 2 years unfiled and the penalties were almost 40% of what I owed! My CPA got most of them removed by showing I had health issues that prevented timely filing.
Good point about penalties. I think with the substitute return already filed, doesn't that mean some penalties are already assessed? Is it harder to get abatement after that point?
One thing nobody's mentioned yet - don't ignore the letter or miss the deadline to respond! Even if you haven't hired help yet, send something in writing acknowledging receipt of their notice and stating that you're in the process of gathering records and seeking professional assistance. I made the costly mistake of missing the 30-day window to contest an IRS assessment, and it severely limited my options after that. At minimum, request an extension while you find representation. You can always do this yourself even before hiring someone.
Thank you for mentioning this! The letter gives me 45 days to respond or file an appeal. Should I just send a simple letter saying I'm gathering documentation and seeking professional help? Or is there specific language I should use?
Yes, send a simple letter acknowledging receipt of their notice (include the notice number) and state that you're gathering documentation and seeking professional representation. Request an extension of time to respond fully - typically 30 or 60 additional days. Keep it professional and straightforward - don't try to argue your case yet or make any specific claims about your tax situation until you have professional guidance. The goal is simply to prevent default assessment while you get your team together. Send it certified mail so you have proof of delivery.
Been through this. For $140k, definitely get a tax attorney first, then let them decide if you need a CPA too. Don't cheap out here - a good tax attorney literally saved me about $70k on a $120k assessment. Make sure whoever you hire specializes in tax controversy/IRS disputes specifically. Regular CPAs who just do tax prep often make things worse in audit situations. Look for someone with at least 10+ years experience dealing with the IRS.
Luca Romano
One thing nobody's mentioned yet - check if the notice you received is actually from the IRS! There are TONS of tax scams that look like official IRS letters. Real IRS notices always have a notice number (like CP501 or LT11) in the upper right corner and always include info about your appeal rights. Never call phone numbers listed in the letter - instead call the main IRS number (800-829-1040) to verify it's legit. And the IRS never demands immediate payment via gift cards, wire transfers, or cryptocurrency, which is a dead giveaway for scams.
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Ravi Gupta
ā¢Thanks for mentioning this! The letter does have a notice number (CP504) and there's info about appeal rights. I looked it up and CP504 is a "Final Notice of Intent to Levy" which is freaking me out even more. Does this mean they're about to take money from my accounts?
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Luca Romano
ā¢A CP504 is indeed a legitimate IRS notice and it's basically warning you that they may levy (seize) your assets or tax refunds if you don't address the debt. However, it's not actually the final notice before levy despite what the title suggests. Before they can actually levy your bank accounts or wages, they must send you a "Final Notice of Intent to Levy and Notice of Your Right to a Hearing" (Letter 1058 or LT11) and give you 30 days to request a Collection Due Process hearing. The CP504 is serious, but you still have time and options before any levies would occur. This would be a good time to contact the IRS to discuss resolution options like a payment plan or making a dispute if you believe the assessment is incorrect.
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Nia Jackson
I've been through exactly this with old tax debt. Here's what worked for me: 1) Get your account transcripts for that tax year 2) File Form 12277 "Application for Withdrawal of Filed Notice of Federal Tax Lien" if they've filed a lien 3) Consider an Offer in Compromise if you can't pay the full amount 4) Look into "Currently Not Collectible" status if you're facing financial hardship The IRS can be reasonable if you're proactive. Just ignoring it is the worst thing you can do. And if you've had major life events like job loss, medical issues, etc., mention those when you contact them - sometimes they take hardship into consideration.
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NebulaNova
ā¢For the "Currently Not Collectible" status, what kind of documentation do they require? I've been unemployed for 9 months and there's no way I can pay my tax debt.
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