Word of advice, NEVER go back to that tax preparer. I'm shocked they would claim that including insurance-paid expenses is legal. That's like Tax 101 stuff. For your audit, be super cooperative with the IRS and explain that you relied on your preparer's expertise. You should definitely request penalty abatement under "reasonable cause" since you hired a professional and had no reason to doubt their work.

Edward, I completely understand your stress about this situation. The good news is that medical expense audit issues are actually quite common and the IRS sees them frequently. Since you questioned your preparer about this approach and she insisted it was correct, you have a strong case for reasonable cause penalty relief. Here's what I'd recommend doing immediately: 1) Gather all your medical bills, insurance EOBs, and payment records from the audit years, 2) Calculate your actual out-of-pocket expenses (what YOU paid after insurance), 3) Prepare amended returns showing the correct deduction amounts, and 4) Write a detailed explanation letter describing how you relied on your preparer's professional advice. The IRS typically works with taxpayers who are cooperative and honest about mistakes, especially when a paid preparer was involved. You'll likely owe additional tax plus interest, but penalties can often be waived or reduced significantly. If you can't pay the full amount, the IRS offers installment agreements - don't let the fear of a large bill prevent you from responding promptly. Also, definitely document any communications you had with your preparer about questioning this deduction method. That evidence will be crucial for your penalty abatement request.

Something nobody's mentioned - if this is your first job ever, you might qualify for some credits that will reduce any taxes you might owe. Did you have any tuition expenses? Moving expenses to get closer to work? Work from home expenses? Also make sure you claim the Climate Action Incentive payment if you live in Alberta, Saskatchewan, Manitoba or Ontario. It's a few hundred bucks you could get back depending on your province!

I went through this exact same stress last year! The good news is that if your employer has been deducting taxes from your paychecks (which it sounds like they have), you're probably in good shape. Here's what helped me figure things out: Get your T4 from your employer - they're required to give it to you by the end of February. This document will show exactly how much you earned and how much tax was already deducted. Since you mentioned your paystubs show tax withholding, you'll likely either owe a small amount or get a refund. For a first job with straightforward employment income, the withholding system usually works pretty well. A few quick tips for first-time filers: - Don't forget to claim the basic personal amount (everyone gets this) - If you moved for work, keep those receipts - moving expenses can be deductible - Any tuition or textbook expenses from school can reduce your taxes - Work-from-home expenses if your job required it The "chicken and egg" problem with the CRA account is super frustrating, but once you file your first return, you'll be able to access your online account for future years. Until then, the tax software options others mentioned will show you exactly what you owe (or what you're getting back) before you submit anything. You've got this! First-time filing is intimidating but it gets much easier once you've done it once.

Quick question - does anybody know if the Section 179 works for used equipment? I'm looking at buying a used commercial oven for my bakery that's about $18,000 (new would be like $30k). Does previously owned stuff qualify?

Great thread! As someone who's been running a small manufacturing business for 8 years, I wanted to add a few practical tips that might help with your food truck situation: First, don't overlook smaller items - things like commercial-grade tablets for inventory management, specialized storage containers, or even heavy-duty extension cords can add up and qualify for Section 179. I've seen people focus only on the big-ticket items and miss hundreds or thousands in smaller deductions. Second, if you're planning that delivery van purchase, consider the timing carefully. Since you mentioned meeting with your accountant next week, ask them about your projected income for the rest of the year. If you're expecting a strong Q4, making the van purchase before December 31st could maximize your tax savings. One thing that caught me off guard my first year using Section 179 - make sure your business structure can handle it. If you're a sole proprietor or single-member LLC, the deduction flows through to your personal return and can only offset business income, not other income sources. Also keep detailed records of everything, including photos of equipment in use at your food truck. The IRS loves documentation, and it'll save you headaches if you ever get audited. Good luck with maximizing those deductions!

Don't forget that when closing your business, you also need to handle any state-level requirements. If you collected sales tax for your Facebook lives or flea market sales, you'll need to file final sales tax returns. Some states also require you to formally dissolve even small businesses. Since you only had an EIN, it's probably minimal, but worth checking your state's requirements to fully close everything out.

One thing that hasn't been mentioned yet - if you're planning to donate any of the unsold crystals to charity instead of selling them, you can potentially deduct the fair market value as a charitable contribution on your personal return (Schedule A). However, you'd still need to remove the inventory from your business books at cost, so you can't double-dip on deductions. Also, make sure to keep detailed records of everything you do with the remaining inventory - whether you sell it, donate it, or convert it to personal use. The IRS may ask for documentation during an audit, and having a clear paper trail of how you disposed of each item will save you headaches later. Take photos of the inventory and keep receipts for any bulk sales or donation acknowledgments from charities. The key is being consistent in your reporting and having documentation to back up whatever method you choose for handling the unsold merchandise.

Has anyone used a TIC (Tenants in Common) arrangement as part of their 1031? I'm in a similar position as OP but might not want to go all-in on another multi-family. I've heard you can exchange into a partial ownership of a larger commercial property.

Based on your numbers, you're looking at roughly $245k in capital gains ($720k sale price - $410k purchase - $65k improvements). Since you've been living in the upstairs unit, you should definitely explore the Section 121 exclusion first. The key question is whether you can document that you've used the upstairs unit as your primary residence for at least 2 of the last 5 years. If so, you could potentially exclude up to $125k of gains (50% of the $250k exclusion for the residential portion) and only need to deal with taxes on the remaining investment portion. Given that your total gain is right around $245k, the combination approach (Section 121 + partial 1031) could work really well. You'd exclude gains on your residence portion and defer the investment portion through the 1031 exchange. For your financing question - yes, a 1.25 DSCR with 20% down is definitely achievable for a 4-6 unit property in that price range, especially if you can show strong rental income history from your current duplex. One thing to consider: make sure you factor in depreciation recapture on the rental portion. Even with a 1031, you'll eventually face that when you sell the replacement property, unless you keep exchanging indefinitely or hold until death for the stepped-up basis.