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.

3 Just to add from my experience as a payroll specialist - most W-2c forms we issue are for small corrections that don't impact federal tax liability. Common ones include: - State tax withholding adjustments - Incorrect address or name spelling - Box 12 code corrections for benefits - Retirement plan checkbox errors Only about 30% of the W-2c forms we issue actually require the employee to amend their return. So don't panic until you see what specifically was corrected!

14 I got a W-2c last year after my company realized they messed up reporting some health insurance premiums. The crazy thing was that even though the numbers changed a bit, my tax software said it didn't affect my refund at all! Apparently some changes just don't matter for tax calculations. Maybe wait to see what exactly changed before worrying too much?

Has anyone actually formed their LLC structure this way, with one disregarded LLC owning another? I'm curious how you handled the paperwork. When filing articles of organization for the second LLC, do you list the first LLC as the member, or do you still list yourself?

This is a great discussion! I've been considering a similar structure for my photography business and a separate e-commerce venture. One thing I wanted to add that hasn't been mentioned yet - make sure you keep meticulous separate records for each LLC even though they're both disregarded entities. The IRS may disregard them for tax purposes, but if you ever face an audit or legal challenge, you'll want crystal clear documentation showing that these are truly separate business activities. Keep separate bank accounts, separate bookkeeping, separate contracts - treat them as completely independent businesses operationally even if they're connected ownership-wise. Also, consider whether you might want to elect S-Corp status for either LLC down the road as your businesses grow. Having the separate entity structure already in place gives you more flexibility for tax planning in the future without having to restructure everything.