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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?
Simon White
ā¢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!
That makes sense. Just wanted to mention it since some people choose MFS without realizing all the limitations. If you're separated and can't coordinate filing jointly, then focusing on getting your fair share of the mortgage interest is definitely the way to go. Good luck with the amendment!
Ally Tailer
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.
That's not entirely accurate. You can't just request someone else's tax information, even an ex-spouse. You only have access to the joint returns you filed together. For years you filed separately, those are protected by privacy laws.
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Something similar happened to me, and I found out it was because I didn't include my SSN on every page of the documents I sent in. Apparently if they can't immediately identify who the paperwork belongs to, it sits in a pile somewhere. When you resend your documentation, make sure your SSN, the tax year, and the notice number appear on EVERY SINGLE PAGE. Also include a copy of the notice itself as the first page of your package. I learned this trick from my aunt who worked at the IRS for 20 years.
That's a great tip! I definitely didn't put my SSN on every page, just on the cover letter and the forms. Do you know if there's any specific format they prefer for this info? Like should it be in the header or just handwritten at the top?
The IRS prefers it in the upper right corner of each page. You can handwrite it or type it, but make sure it's clear and includes both the SSN and the tax year in question. Something like "SSN: XXX-XX-XXXX Tax Year: 2021" is perfect. Also, don't staple anything! Use paper clips if you need to keep pages together. Staples slow down their processing because they have to remove them to scan everything.
Zara Ahmed
Has anyone mentioned the Taxpayer Advocate Service yet? They can sometimes help in situations like this where there's been an obvious breakdown in normal IRS processes. They won't represent you like a tax attorney, but they can often cut through red tape and get someone at the IRS to actually look at your case. They're free to use and pretty effective for situations exactly like yours. Google "Taxpayer Advocate Service" + your state to find the contact info for your local office.
StarStrider
ā¢TAS has been swamped since the pandemic. I tried using them last year and they told me they were only taking "hardship" cases where people were facing immediate financial harm. Worth a try though!
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Kevin Bell
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.
Kevin Bell
ā¢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.
Felicity Bud
ā¢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?
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Omar Fawzi
You might want to look into whether you qualify as a "trader" vs an "investor" for tax purposes. If you're doing enough volume and frequency of trades, you might be able to elect the "mark-to-market" accounting method which treats all your securities as if sold on the last day of the tax year. This gives you ordinary gain/loss treatment rather than capital gains and eliminates the wash sale rule concerns. But there are strict requirements and you need to make the election in advance. Worth talking to a tax professional about it.
Chloe Wilson
ā¢How many trades do you need to do to qualify as a "trader" for the IRS? I do about 20-30 trades a month. Is that enough?
Omar Fawzi
ā¢There's no specific number that automatically qualifies you. The IRS looks at several factors: trading frequency (daily is best), holding periods (shorter is better), time devoted to trading (more is better), and whether you depend on the income. Your 20-30 trades monthly might be enough if they're your primary activity and you hold positions briefly. The courts have generally supported trader status for those doing hundreds of trades annually, spending several hours daily on trading, and holding positions for very short periods. But it's a facts-and-circumstances test, not just a number threshold. I'd recommend consulting a tax pro who specializes in trader taxation since the benefits can be substantial but the requirements are strict.
Has anyone used TurboTax for reporting a lot of trades? My broker sent me a consolidated 1099 with like 200+ trades and I'm wondering if I need to enter each one manually or if there's a way to import them.
Most brokers can export your trades in a format TurboTax can import. Look for a .TXF file export option on your broker's tax documents page. If they don't offer that, you might be able to download your transactions as a CSV and convert it using a third-party tool.
Thanks for the tip! Just found the .TXF export option on my broker's website. That's going to save me hours of manual data entry. I was dreading having to type in all those trades one by one.
ThunderBolt7
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!
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Jamal Edwards
ā¢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.
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ThunderBolt7
ā¢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!
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Mei Chen
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.
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Nia Williams
ā¢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.
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