Has anyone else noticed that the 1099-NEC instructions are super unclear about family care situations? I read through them twice and still couldn't figure out if my mom's caregiver payments needed to go on Schedule C or not.

Based on the details you've provided, it sounds like your family care company should issue 1099-NEC forms rather than 1099-MISC. The NEC form is specifically for non-employee compensation for services, which is what you're receiving - compensation for caregiving services you'll provide to your dad. For tax reporting, since this is a one-time payment for occasional family caregiving (not a regular business you operate), you would likely report this income on Schedule 1 of Form 1040 as "Other Income" rather than on Schedule C. This means you wouldn't owe self-employment tax on this payment. The key factors supporting this treatment are: 1) You don't do caregiving as a regular business, 2) It's a one-time payment rather than ongoing regular income, 3) The services are flexible family support rather than structured business activities, and 4) You're all retired/employed in other fields. However, given the complexity of your family's legal and financial arrangement, I'd strongly recommend confirming this with a tax professional who can review all the specifics of your situation. The distinction between casual family help with compensation versus operating a caregiving business can have significant tax implications.

I did exactly what you're asking about last year and ended up getting a notice from the IRS. Had to refile and pay penalties plus interest. Even my accountant missed this! S-corp owners HAVE to be W-2 employees if they're performing services. end of story.

Just wanted to chime in as someone who made this exact mistake when I first started my S Corp. I thought I was being clever by avoiding payroll taxes, but it backfired spectacularly. The IRS has very specific rules about S Corp shareholder-employees - if you're providing services to the corporation (which you clearly are as an IT consultant), you MUST be treated as an employee with proper W-2 wages. The "reasonable salary" requirement exists specifically to prevent what you're thinking about doing. The whole point of an S Corp is that you pay employment taxes on your salary, then take additional profits as distributions (which aren't subject to SE tax). If you could just pay yourself as a contractor, everyone would do it to avoid payroll taxes entirely. My advice: set up proper payroll for yourself immediately. Yes, it's more paperwork and you'll pay both sides of payroll taxes on your salary portion, but it's the only compliant way to do this. The tax savings on your distributions will more than make up for it, and you'll avoid the audit risk and penalties that come with trying to game the system.

Has anyone else noticed that the HSA contribution limits for 2020 are way lower than 2023? I just saw that for 2023 they're $3,850 individual and $7,750 family. Wish they'd bump these up more aggressively with inflation - healthcare costs are insane these days!

This is a really helpful thread! I'm in a similar situation but with a twist - I'm 24 and on my dad's HDHP, but I also have a part-time job that offers an HSA. My employer keeps telling me I can contribute the family amount since I'm "on a family plan," but based on what everyone's saying here, that sounds wrong. It seems like the consensus is that since I'm only covering myself (even though I'm on someone else's family plan), I should only be able to contribute the individual limit of $3,550 for 2020. Is that right? I'm worried my employer's HR department is giving me bad advice and I'll end up with penalties. Also, does it matter that my dad probably isn't contributing to an HSA at all? He's not really into that stuff and just uses the insurance for basic coverage. Would that change anything about my contribution limits?

OP I've been a full-time youtuber for 3 years now and the biggest mistake I made was trying to DIY my taxes the first year. Even with all the online advice, I missed so many legit deductions and probably overpaid by thousands $$$. My advice: find a CPA who works with content creators specifically. Regular tax preparers often don't understand our weird mix of expenses and income streams. Might cost $300-500 for tax prep but you'll likely save way more than that in deductions they'll find that you'd miss.

Just my two cents - be careful with deducting things you haven't used yet. My brother got audited last year for his small business and the IRS was particularly interested in equipment he'd purchased but hadn't deployed in his business yet. He ended up having to prove he had a legitimate business need for the items at the time of purchase. He had emails and business plans showing his intent, so he was fine, but it was definitely a stressful experience.

One thing I haven't seen mentioned yet is keeping detailed records of your cleanup and restoration costs too. After Hurricane Michael, I learned that reasonable costs for cleaning, repairs, and even temporary storage while dealing with the damage can sometimes be included in your casualty loss calculation. Also, if you're dealing with contaminated floodwater like you mentioned (sewage backup), make sure to document any health-related expenses from exposure. While medical costs aren't part of the casualty loss itself, they might be deductible as medical expenses if they exceed the threshold. For your antique valuation issue, consider reaching out to local auction houses or estate sale companies. Many of them can provide informal estimates based on photos, and having that professional opinion documented in writing adds credibility to your claim. Even if it's not a formal appraisal, it shows you made a reasonable effort to establish fair market value. The key is showing the IRS that you acted in good faith and used reasonable methods to determine values. Your photos of the damage are actually really valuable evidence that many people forget to take, so you're ahead of the game there.

I want to add something important about the sewage contamination aspect that hasn't been fully addressed. When floodwater contains sewage (which you mentioned), the IRS actually allows you to claim the full replacement cost for certain contaminated items rather than just fair market value, since they're considered a health hazard that can't be properly cleaned. This is particularly relevant for your clothing, mattresses, and upholstered furniture that were soaked in contaminated water. For these items, you can often claim what it would cost to replace them with similar items today, not just their depreciated value before the hurricane. This can significantly increase your deductible loss. You'll want to clearly document which items were exposed to sewage contamination versus clean floodwater. Take photos that show the water line and any visible contamination, and keep records of any professional recommendations you received about disposal of contaminated items. Also, regarding your FEMA payment - make sure you understand exactly what it covered. If FEMA designated some of that $1,350 for specific items (like temporary housing assistance), those amounts might not reduce your casualty loss for different categories of property. You should have received documentation from FEMA breaking down what the payment was intended to cover. Have you considered consulting with a tax professional who specializes in disaster losses? Given the complexity with the sewage contamination and the mix of antiques and regular household items, it might be worth the cost to ensure you're maximizing your legitimate deductions while staying compliant.