I'm surprised nobody mentioned that you might want to prioritize the more recent tax years first. The IRS generally has a 3-year statute of limitations for audits and amendments, so 2019 might be cutting it close depending on when you filed.

I went through this exact same situation two years ago and can confirm what others have said - it's not as scary as it seems! I had about $35,000 in unreported backdoor Roth conversions from 2018-2021. Here's what I learned: First, definitely prioritize getting 2019 fixed ASAP since you're approaching the 3-year statute of limitations. Second, the IRS was actually pretty understanding when I explained it was an honest mistake about reporting requirements. The key thing that helped me was keeping detailed records showing the timeline: contribution date, conversion date (hopefully very close together), and the exact amounts. This proves you did a legitimate backdoor Roth and weren't trying to hide anything. I ended up owing about $47 total across all years - just tax on the small gains that occurred between contribution and conversion (like $2-3 per conversion). No penalties since I proactively corrected it and included a reasonable cause letter explaining I misunderstood the Form 8606 requirement. The whole process took about 6 months to fully resolve, but the peace of mind was worth it. Don't let this keep you up at night - just get started on those amended returns!

Does anyone know if receiving a 1099-NEC automatically makes you eligible for the home office deduction? I'm in a similar situation - side consulting gig, but I sometimes work from coffee shops or the library too, not just my home office.

Just want to add that I went through this exact situation last year with my freelance graphic design work. The key thing that helped me was creating a clear floor plan diagram showing exactly which part of my spare room was used exclusively for business (just my desk area and immediate workspace, not the whole room since I had personal storage there too). I also kept a simple business activity log for a few months showing what work I did in that space - client calls, design work, invoicing, etc. This helped establish the "regular use" part of the requirement. Even though I only worked 8-10 hours a month on this side business, I was able to take the deduction because that space was 100% dedicated to business use. One tip: measure carefully and be conservative. I actually had my office area professionally measured to make sure I wasn't overstating the square footage. Better to slightly underestimate than risk issues later. The peace of mind was worth it for the relatively small amount I might have "left on the table.

Have you considered the potential penalties you might face? I just went through something similar and ended up owing about 20% on top of the additional taxes, plus interest dating back to the original filing deadline for each year.

This is a serious situation that unfortunately happens more often than people realize. As someone who works in tax compliance, I've seen cases where preparers inflate deductions thinking they're "helping" clients, but they're actually putting them at significant risk. Your instinct to be concerned is absolutely correct. The fact that you have such large discrepancies ($2,700 vs $800 and $13K vs $3K) suggests this wasn't just aggressive but legitimate tax planning - these sound like fabricated deductions. Here's what I'd recommend: First, document everything. Gather all your actual business expense records for those years so you have concrete evidence of what your real expenses were. Then have that conversation with the CPA - ask specifically what documentation they used for each major deduction category. Their response will tell you everything you need to know about whether this was intentional. If they can't provide reasonable explanations or documentation, you should absolutely file amended returns. Yes, you'll owe additional taxes plus interest, but voluntary correction shows good faith and typically avoids fraud penalties. The alternative - waiting and hoping you don't get audited - is much riskier. The IRS takes a dim view of preparers who fabricate deductions, and if this was intentional, other clients are likely affected too. After you get your own situation sorted, consider whether reporting is appropriate.

Has anyone dealt with Section 754 elections when a partnership interest changes hands? We did a family buyout last year and our accountant mentioned it but I'm still confused how it works.

Great discussion everyone! Just wanted to add one more consideration that might be relevant - timing of the sale within the tax year can matter quite a bit. If your friend sells early in the partnership's tax year, he'll have a shorter period of K-1 income to deal with, but the family members will have their increased ownership percentages for most of the year. Also, make sure they consider whether the partnership needs to file an amended partnership agreement or operating agreement to reflect the new ownership structure. While this isn't directly a tax form, having the legal documentation updated will make future tax filings much cleaner and help avoid any questions from the IRS about ownership percentages on future K-1s. The partnership should also notify their tax preparer about the ownership change as soon as it happens so they can properly allocate income and expenses for the partial year periods on everyone's K-1s.

Another option is using a mileage tracking app like MileIQ or Everlance throughout the year. They automatically track your trips using GPS and let you swipe left/right to categorize as business or personal. At tax time, you can just export a summary report for your records and enter the total in TurboTax as one line item. Much easier than spreadsheets!

Has anyone had experience getting audited specifically for mileage deductions? I'm always paranoid about claiming too much even though I drive a ton for my job.