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Something nobody has mentioned yet is that you'll need to be really careful about the 45-day identification period and the 180-day completion period for the 1031 exchange portion. Miss those deadlines and you lose the tax deferral completely. Also make sure your qualified intermediary is bonded and insured - I learned that lesson the hard way when my first QI went bankrupt while holding my exchange funds...
How did you handle the QI bankruptcy situation? Were you able to recover your funds or did you end up having to pay the capital gains?
I was extremely lucky that the bankruptcy happened on day 15 of my 45-day identification period. I immediately hired a new QI who was able to make a claim against the first QI's bond. I did recover about 85% of my funds eventually, but it delayed my purchase of the replacement property and caused a ton of stress. I ended up having to bring additional cash to closing to make up the difference. The bigger problem was that I nearly missed the 180-day deadline for completing the exchange because of all the legal complications. If that had happened, I would have owed tax on the full gain. Now I only use large, established QI companies that have significant insurance and bonding, even if they charge slightly higher fees.
Question for anyone who's done this successfully - what documentation do you need to support the allocation between personal and investment use? Do you just claim 50/50 for a duplex or do you need to measure actual square footage? And what about shared spaces like a basement or driveway?
I did this last year with a triplex (lived in one unit, rented two). My CPA had me use square footage as the most defensible method in case of audit. We calculated the percentage of the total square footage that my unit represented, then allocated purchase price, improvements, and selling costs accordingly. For common areas, we split those proportionally too. Keep VERY detailed records of when you converted part to personal use, any improvements made to either side, and maintenance costs. Take photos of everything. The more documentation you have, the better position you'll be in if the IRS questions your allocation.
Something similar happened at my workplace. For clarification - did your job duties change at all when they made this switch? Or did everything stay the same except how they paid you? Because that's a huge red flag. Also, do you receive directions from your boss, use their equipment, work set schedules, etc? Those are all signs you're an employee not a contractor. Your employer can't just decide to stop withholding taxes because they don't want to deal with the paperwork for part-timers.
Nothing about my job changed at all - same duties, same desk, same boss giving me the same tasks and schedule. The only difference is they stopped withholding taxes and then sent me this 1099 instead of a W-2. I use all their equipment, work entirely on-site, and have zero control over my hours or how I complete my work.
Yeah, that's textbook misclassification then. They can't just arbitrarily decide to treat you as a contractor while maintaining all the control of an employer relationship. They're doing this to save money on their end (employer-side taxes, benefits, etc.) while shifting the tax burden to you. I'd recommend documenting everything about your work arrangement - hours, supervision, equipment, etc. Then either talk to your employer about correcting this (if you think they'd be receptive) or follow the advice others have given about filing SS-8 and 8919 forms with the IRS.
Quick question - did your pay rate increase when they switched you to 1099? Because if not, you're effectively taking a 7.65% pay cut since you're now responsible for the employer portion of FICA taxes. Many employers who do this "conversion" properly will increase the hourly rate to offset the tax difference.
Not just 7.65% - it's more like 15.3% total for self-employment tax! Half would normally be paid by the employer, and half would be withheld from your paycheck. So if your pay didn't increase AT ALL, you're taking a massive hit.
Long-time tax preparer here - just a quick tip about form 1096 corrections: if your correction changes the TOTAL amount you're reporting substantially, it's worth including a brief cover note explaining the correction. This isn't required, but it helps prevent questions later. For example, if you're correcting a total from $10,000 to $100,000, that's the kind of change that might raise flags during processing.
What's considered "substantial" though? Is there a percentage or dollar amount threshold where you should include an explanation?
There's no official threshold, but I generally use 10% or $1,000 (whichever is greater) as my rule of thumb. So if you're correcting an amount from $5,000 to $5,500, that's probably not significant enough to need explanation. But if you're changing from $5,000 to $7,500 or more, I'd include a brief note. The key is anticipating what might make a processor pause when reviewing your forms. Large dollar amount changes or corrections that affect the fundamental purpose of the form are worth explaining briefly.
Random question - can I use blue ink for the correction or does it have to be black? I know the IRS is picky about some of these details.
Another option that might work - have you tried contacting the tax preparer who did your amended return? If you used a professional, they should have kept a copy of everything they filed for you, including the 1040X with the date. If you used tax software, you might be able to log back in and reprint the form.
I actually prepared and filed the 1040X myself using paper forms because the amendment was pretty simple - just correcting an education credit amount. So I don't have a preparer to contact. And I do have the physical copy, it's just missing the date in the signature section, which apparently is a deal-breaker for my financial aid office. They're super strict about having complete documentation.
That's unfortunate. In that case, I think your best options are what others have suggested - either visiting a Taxpayer Assistance Center in person for immediate help or using one of the services mentioned to get through to the IRS more efficiently. Since you mentioned your deadline is approaching, I'd probably pursue multiple options simultaneously. Start the process with taxr.ai since that seemed to work for someone else with your exact issue, but also try to schedule an in-person appointment at a TAC as a backup plan.
Has anyone else noticed that the IRS seems to be getting even harder to deal with recently? Last year I could at least get through to a person after about 45 mins on hold, but now it's like they don't even pick up at all.
I heard they're severely understaffed and dealing with massive backlogs still. My cousin works for the IRS and says they're processing literally millions of paper forms with too few employees. Apparently the best times to call are early Tuesday, Wednesday or Thursday mornings right when they open.
Thanks for the tip. Maybe I'll try calling at 7am on Tuesday and see if that helps. It's just frustrating that they make it so difficult to get basic documents that we're legally required to have.
Ruby Knight
One thing nobody's mentioned yet - make sure you file ALL missing returns at once. Don't file just the most recent year thinking you'll do the rest later. The IRS wants to see you completely back in compliance. Also, if you can pay even part of what you owe when you file, it shows good faith and can sometimes result in reduced penalties. I was in a similar situation (3 years unfiled) and managed to pay about 30% upfront, which helped tremendously with negotiating the rest.
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Ella rollingthunder87
ā¢Is there a statute of limitations on how far back they can come after you for unfiled taxes? I'm worried they'll want returns from like 10 years ago even though I wasn't making much money back then.
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Ruby Knight
ā¢The statute of limitations for the IRS to assess taxes is generally 3 years from the date you file your return. However - and this is important - there is NO statute of limitations on unfiled returns. The clock doesn't start until you actually file. For your situation, they typically focus on the last 6 years for unfiled returns, but technically they could go back further. That said, if you weren't making much money in those earlier years, it might not be worth their effort. My tax preparer advised me to focus on the last 6 years, but your situation might be different.
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Diego Castillo
Don't forget about state taxes too! Everyone's talking about the IRS, but your state tax authority might be even more aggressive about collection. Make sure you're addressing both federal AND state unfiled returns.
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Logan Stewart
ā¢This is so important. My brother dealt with the IRS fine on his back taxes but completely forgot about state taxes. California actually put a lien on his property before he even knew what was happening.
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