Has anyone considered using a charitable remainder trust to avoid the capital gains tax? I'm looking at a similar situation with a property that's appreciated a ton and my financial advisor mentioned it but i'm not sure if it's legit or too complicated.

One thing that hasn't been mentioned yet is the depreciation recapture issue. If you ever claimed any depreciation deductions on this vacation condo (maybe if you rented it out occasionally), you'll owe depreciation recapture tax at 25% on that amount before the capital gains rates apply to the remaining gain. Also, make sure you're factoring in selling costs like realtor commissions, title insurance, and legal fees - these can be subtracted from your gain calculation. For a $775k sale, you're probably looking at $30-50k in selling expenses which reduces your taxable gain. Given the size of your potential gain ($525k+), I'd strongly recommend getting a tax professional involved regardless of which strategy you pursue. The 1031 exchange has strict timelines and the vacation home conversion strategy has complex calculations that can trip you up if not done correctly.

Great breakdown of the pricing differences! I went through a similar comparison last year and was shocked at how much I was overpaying with the big-name services. One thing I'd add is to watch out for the upselling tactics during the filing process. H&R Block and TurboTax are notorious for starting you on their "free" tier and then gradually pushing you toward premium features you probably don't need. FreeTaxUSA is much more upfront about what costs extra, and their base paid tier covers most situations without the constant upgrade prompts. The only scenario where I might consider paying more is if you have a really complex tax situation with multiple rental properties, foreign income, or complicated business structures. But for the vast majority of people filing standard W-2s with some basic investments and deductions, you're absolutely making the smart choice going with the cheaper option.

Completely agree with your choice! I made the same switch two years ago and haven't looked back. The price difference is absolutely ridiculous for what you get. One thing I learned is that most of these tax software companies are literally using the same underlying tax calculation engines - they're all just different interfaces wrapped around the same IRS forms and tax code. So you're essentially paying $80+ extra for flashier graphics and brand recognition. I also appreciate that FreeTaxUSA doesn't bombard you with constant upsells during the filing process. With H&R Block, I felt like I was being pitched something new every other screen - "premium support," "maximum refund review," "audit protection" - most of which are unnecessary for straightforward returns like yours. The only people I know who still use the expensive services are either those with very complex business situations or folks who just haven't realized there are better alternatives. For standard W-2 employees with basic investments and deductions, FreeTaxUSA is definitely the way to go.

Has anyone had luck deducting part of their cell phone bill for delivery work? I use my phone constantly for the apps, GPS, customer communication etc.

Great question! Yes, you definitely should be tracking your mileage for 1099 delivery work - it's one of the biggest deductions you can take. Here's what I recommend: **For odometer readings:** You don't need to record it for every single trip, but do take photos of your odometer at the beginning and end of each work day, plus at the start/end of each year. This gives you solid documentation. **What to track for each delivery:** - Date and time - Starting point and destination - Miles driven (business purpose) - Total miles for the day **Pro tip:** Stop estimating immediately! The IRS can be strict about mileage deductions, and estimates won't hold up in an audit. Either use a mileage tracking app (like Stride, Everlance, or MileIQ) or keep a simple log in your car. You can choose between the standard mileage rate (67¢/mile for 2024) or actual vehicle expenses - the standard rate is usually better for delivery drivers and much simpler to track. Since you just started last month, you can still go back and reconstruct your mileage using your delivery app records, bank statements, and any receipts you have. Better to get organized now than scramble at tax time!

One thing nobody's mentioned yet - if part of your HSA distribution was used for non-medical expenses, you'd only pay the penalty on that portion. For example, if $1500 of your distribution was for medical stuff but $350 was for something else, you'd only pay the penalty on the $350. I learned this the hard way last year when I accidentally used my HSA debit card for some regular pharmacy items that weren't medical (like paper towels and snacks along with my prescriptions). Had to pay extra tax but only on those specific non-qualified items.

This is a classic HSA reporting mistake that catches a lot of people! The dramatic jump in your tax bill is happening because your tax software is treating your entire $1,850 distribution as taxable income PLUS adding the 20% penalty for non-qualified distributions. Here's what's likely happening: When you entered your 1099-SA, you probably missed indicating that the distributions were for qualified medical expenses. Without that designation, the software assumes it was a non-qualified distribution and hits you with: 1. Regular income tax on the full $1,850 2. An additional 20% penalty tax (another $370) That explains your ~$810 jump in taxes owed ($1,590 - $780). Go back to your HSA section in your tax software and look for questions about whether the distribution was used for qualified medical expenses. Since you mentioned having receipts for doctor visits, prescriptions, and a procedure, you should be able to mark these as qualified distributions. Once you do that, your tax bill should drop back down significantly since qualified HSA distributions are completely tax-free. The key is making sure your software knows these were legitimate medical expenses!

You're absolutely doing the right thing by maintaining your boundaries. As someone who's dealt with similar accounting disasters, I can tell you that a $340k retained earnings discrepancy with phantom assets and missing liabilities is not a part-time bookkeeping project - it's a full-scale forensic accounting engagement. The fact that the previous admin was making changes to closed years is particularly alarming from a compliance perspective. This suggests potential issues with previously filed returns that could trigger audit exposure. Here's my suggested approach: Create a detailed findings memo that includes (1) specific examples of the major discrepancies you've found, (2) an honest assessment that this requires 200-300+ hours of specialized work, and (3) a strong recommendation to engage a CPA firm experienced in multi-year accounting reconstructions. Don't feel guilty about saying no. You were hired for current operations, not to fix years of accumulated errors at below-market rates while managing health challenges. Your responsibility is to identify problems and recommend appropriate solutions - which you've done. The owner needs to understand this isn't about unwillingness to help, it's about ensuring the work gets done properly by someone with the right expertise, capacity, and professional insurance to handle this level of complexity. A botched reconstruction attempt could make things worse, not better. Document everything, make your recommendations clear, and help them find qualified professionals. That's the most responsible path forward for everyone involved.

You're in an absolutely impossible situation, and I completely understand the guilt you're feeling. But you need to remember - you didn't create this mess, and you're not responsible for fixing 6 years of accumulated errors, especially given your health limitations and part-time status. A $340k retained earnings discrepancy is not a "cleanup" - it's a full forensic reconstruction project. When you have phantom assets, missing liabilities, and evidence that someone was making changes to closed years, you're looking at potential tax compliance violations that could have serious consequences. Here's what I'd do: Create a comprehensive written report documenting every major issue you've identified. Include specific examples (like that $80k double-counted expense), categorize the types of errors, and provide a realistic scope estimate. Then recommend they engage a CPA firm that specializes in business tax reconstruction - not general bookkeeping, but specifically multi-year tax compliance cleanup. Make it crystal clear that this is a separate professional engagement requiring specialized expertise, appropriate insurance coverage, and significantly more hours than your part-time schedule allows. You were hired to handle current operations, not to perform forensic accounting on years of accumulated mistakes. Your job is to identify problems and recommend solutions - which you've done perfectly. The owner's job is to invest in proper professional remediation. Don't let guilt push you into taking on work that could compromise your health or professional standing.