Has anyone had issues with property taxes being reported incorrectly on these 1098 forms after a loan transfer? My new servicer didn't report any of the property taxes paid through escrow, but the old one did. Trying to figure out if I need to get a corrected form.

This is exactly the situation I found myself in last year! The stress of trying to figure out which numbers to use was keeping me up at night. What really helped me was creating a simple spreadsheet where I listed every mortgage payment I made throughout the year with the dates and amounts, then compared that to what each 1098 form was reporting. I discovered that my original lender was including some fees in their interest calculation that weren't actually deductible interest, while my new servicer had the cleaner numbers. The key is to focus on what you actually paid in mortgage interest, not necessarily what the forms say if there are discrepancies. Also, don't stress too much about triggering an audit - mortgage interest reporting issues are super common and the IRS sees this all the time. As long as you're being honest about what you actually paid and can document it, you'll be fine. Keep copies of all your payment records and mortgage statements just in case you need them later!

I switched from H&R Block to FreeTaxUSA last year specifically because of K-1 issues. H&R Block kept trying to upsell me every time I entered certain trust distributions, and their customer service couldn't even explain why some of my Box 14 codes weren't being accepted. FreeTaxUSA handled my deceased father's trust K-1 without any problems. The software automatically recognized all the codes and guided me through each entry. What really impressed me was that it caught a potential error where I almost double-counted some income that was reported on both a 1099 and the K-1. The interface isn't as fancy as H&R Block, but for complex returns with trusts and multiple income sources, FreeTaxUSA is way more reliable. Plus their customer support actually understands tax law instead of just trying to sell you upgrades.

I've been using FreeTaxUSA for the past three years after getting fed up with similar upgrade tactics from TurboTax. For trust K-1s specifically, FreeTaxUSA is fantastic - it handles all the Box 14 codes without any artificial limitations or surprise fees. One thing that really helped me when I first switched was calling their customer support during my first year with a complex trust situation. Unlike H&R Block's sales-focused support, FreeTaxUSA's team actually walked me through the K-1 entry process and explained what each section was doing. They even caught an issue where I was entering passive activity codes incorrectly. The audit support question is valid, but honestly, most audit protection services from tax software companies are pretty limited anyway. They mainly just provide guidance and won't represent you before the IRS. If you're worried about audit risk with trust income, it might be worth consulting with a CPA for the first year to make sure everything is properly reported, then you can use FreeTaxUSA confidently going forward.

One thing nobody's mentioned - if your LLC is set up correctly, have you considered having the business take out a loan, then personally guaranteeing it? Rates might be higher, but you avoid the retirement tax hit entirely. Also, the interest would be deductible as a business expense.

Another option worth exploring is equipment financing specifically - many lenders offer competitive rates for business equipment purchases, and you can often finance 80-100% of the equipment cost with the equipment itself as collateral. This keeps your retirement funds intact while still getting the equipment you need. I'd also suggest running the numbers on tax-adjusted returns. That 300% return over 8-10 years might look different when you factor in the immediate tax hit from the withdrawal (potentially 22-32% depending on your bracket) plus the 10% penalty if you're under 59½. Don't forget to account for lost compound growth on those retirement funds over the same period. If you do decide to proceed with the withdrawal, consider timing it strategically - maybe split it across two tax years to avoid bumping into a higher bracket, or coordinate with other business expenses to maximize your deductions in the withdrawal year.

This is exactly the kind of situation where proper planning and documentation from day one makes all the difference. I went through a similar analysis when I was considering aircraft investment, and here's what I learned: The IRS looks at several factors beyond just hours worked - they want to see genuine business decision-making authority. Things like approval rights for maintenance expenditures, involvement in setting charter rates, decisions about aircraft availability, and participation in marketing strategies all strengthen your material participation case. One often overlooked aspect is the "regular, continuous, and substantial" requirement. It's not just about hitting 500 hours annually - the IRS wants to see consistent involvement throughout the year, not just seasonal bursts of activity. I'd recommend establishing weekly check-ins with your charter operator and documenting operational decisions you make. Also, consider the economics beyond depreciation. Make sure your projected income from the charter arrangement, combined with any personal use value, creates a legitimate profit motive. The IRS gets suspicious when tax benefits significantly exceed actual economic returns from the activity. Your CPA's caution about audit risk is well-founded, but with proper structure and documentation, aircraft depreciation can be defensible. The key is treating this as a real business operation, not just a tax strategy. Document everything, stay actively involved, and make sure the numbers make sense as a business venture independent of tax considerations.

This thread has been incredibly helpful! As someone who's been considering a similar aircraft investment, I'm grateful for all the practical advice shared here. One area I'd love more clarity on is the relationship between personal use and business classification. If I'm planning to use the aircraft maybe 20-30% of the time for personal trips, does that automatically disqualify me from taking full depreciation? Or is it more about documenting the business percentage and only claiming depreciation on that portion? Also, has anyone dealt with the IRS questioning the fair market value of lease payments to related charter companies? I'm concerned about getting the pricing right - too high might look like you're inflating income, but too low could suggest it's not a legitimate business arrangement. The documentation requirements everyone's mentioned seem extensive but doable. I'm particularly interested in the quarterly business review idea - seems like a great way to create a paper trail of ongoing management decisions while also ensuring the investment is performing as expected.

You need to look into the "Financial Disability" exception to the 3-year refund statute. Under Internal Revenue Code 6511(h), the statute of limitations can be suspended during periods when a taxpayer is unable to manage financial affairs due to a medical condition - and death certainly qualifies. You'll need to file Form 1040X for the unfiled years with "Financial Disability" noted at the top, along with documentation of your father's date of death and an explanation. In my experience, you'll want to attach medical records showing any illness leading up to death if applicable.

I went through something very similar when my father passed in 2021. The key thing that helped me was understanding that the IRS has different rules for deceased taxpayers, especially when notices were sent after death. First, definitely file those 2020 and 2021 returns immediately, even if you're past the 3-year window. Include Form 1310 with each return and a detailed cover letter explaining that your father died in November 2022 and you only recently discovered these unfiled returns during estate administration. For the interest abatement, file Form 843 specifically citing IRC 6404(e)(1) - reasonable cause due to death. The IRS often grants these when they can verify notices were sent to a deceased person's address. Most importantly, request that any refunds from 2020/2021 be applied directly to the 2019 balance rather than issued as checks. Even if the refunds are technically "expired," the IRS can often still use them to offset other tax debts when there are special circumstances like death. I also recommend calling the Practitioner Priority Service line if you have a POA on file - they're more equipped to handle complex estate situations than the regular customer service lines. Document everything in writing and keep copies of all correspondence. The process took about 6 months in my case, but we ultimately got the balances resolved and most of the interest abated. Don't let them tell you there's nothing that can be done - deceased taxpayer cases have more flexibility than they initially let on.