Just to clarify something that might be confusing from the other responses - you absolutely DO need to report that $1,200 as taxable income on your federal return, regardless of whether you itemize deductions or take the standard deduction. The gambling winnings get reported as "Other Income" on your 1040. The loss deduction piece is separate and optional - you can only deduct gambling losses if you itemize deductions AND only up to the amount of your winnings. So if you normally take the standard deduction (which most people do), you'd pay taxes on the full $1,200 and wouldn't be able to deduct that $300 loss. Make sure you received the W-2G form from the casino when you collected your winnings - they're required to give it to you at the time of payout for slot wins of $1,200 or more. You'll need that form to complete your tax return. If you didn't get it or lost it, contact the casino's player services department to get a copy.

One thing that helped me when I was in a similar situation was keeping track of the exact time and date of both my losses and winnings during that casino visit. Since you mentioned losing $300 before hitting the $1,200 jackpot all in the same trip, you might want to check if your player's club card tracked those transactions automatically. Many casinos keep detailed records of your play when you use their rewards card, and you can often request a win/loss statement from them that shows all your activity for that day. This can serve as official documentation for both your winnings and losses, which is really helpful if you do decide to itemize deductions. Even if you end up taking the standard deduction, having that documentation is good to keep for your records in case the IRS ever has questions about your return. Also, don't forget that if any taxes were withheld from your winnings (which sometimes happens on larger jackpots), that information should be on your W-2G form and you can claim those withholdings as payments made toward your tax liability.

Has anyone actually gotten an IRS penalty for HSA over-contributions before? I'm wondering how strict they are about this stuff. I think I might have over-contributed last year but never fixed it and haven't heard anything.

I went through something very similar last year! You're absolutely right that you can still contribute that $150 to get back to your maximum allowable contribution for 2024. As others mentioned, you have until April 15th, 2025 to make 2024 HSA contributions. One thing I'd add is to keep really good records of all these transactions. I created a simple spreadsheet tracking: original contributions, the excess amount, withdrawal date and amount, and then the corrective contribution. This made tax filing much easier and gave me peace of mind if the IRS ever had questions. Also, don't stress too much about the "return of excess contributions" form you already filed - that was correct for the portion that was actually excess. The additional $150 you're putting back in is just you using up your remaining contribution room for 2024, which is totally separate and allowed. Just make sure when you contribute that $150 with Fidelity, you explicitly designate it as a 2024 contribution in their system. Their interface makes this pretty clear during the contribution process.

19 Has anyone here dealt with self-employment taxes when transitioning from employee to owner of an S corp? I'm in a similar situation and confused about whether I should be paying self-employment tax on all business profits now or just my salary portion?

Great discussion here! I went through a similar S corp ownership transfer from my uncle about 18 months ago and wanted to share a few additional considerations that came up during my experience. One thing that caught me off guard was the potential impact of any outstanding business loans or debts that transferred with the ownership. If your dad had any business loans that you assumed as part of the purchase, this can affect your stock basis calculations in ways I didn't initially understand. Make sure your accountant reviews any debt assumptions as part of the transfer. Also, if the business has accumulated earnings and profits (E&P) from before it elected S corp status, or if it was previously a C corp, there could be some built-in gains tax implications down the road. This is pretty technical stuff, but worth asking about since family transfers sometimes involve businesses that have been around for decades. The reasonable salary discussion above is spot on - I ended up having to adjust mine upward after my first year because I was being too conservative. Better to err on the side of paying yourself fairly from the start rather than having to explain to the IRS later why you were trying to minimize payroll taxes. One last tip: keep detailed records of everything related to the transfer. The IRS loves documentation, especially for family business transactions where they might be more scrutinizing of the terms and pricing.

I went through this exact situation and learned the hard way that insolvency at the time of forgiveness is super important! If your dad's liabilities exceeded his assets at the time the debt was forgiven, he might qualify to exclude some or all of the forgiven debt from income. Form 982 is what you'd use to claim this exclusion. This form has to be filed with the tax return, so even if your dad normally doesn't file, he might need to if he wants to claim insolvency.

This is a really complex situation, but you're asking the right questions! Since your dad is on permanent disability and typically doesn't file taxes, the key thing to understand is that any tax implications from the repossession would follow the legal ownership of the loan - which is in his name. One important point that hasn't been fully addressed: even if your dad receives a 1099-C, he may not need to file a return if his total income (including the forgiven debt) still falls below the filing threshold for his age and filing status. For 2023, if he's under 65 and his gross income is less than $13,850 (or $15,700 if 65 or older), he generally wouldn't need to file. However, if the forgiven debt amount is large enough to push him over the filing threshold, he would need to file - but that's where the insolvency exclusion on Form 982 could come into play if his debts exceeded his assets at the time of forgiveness. The fact that you used the car for commuting doesn't create any tax obligations for you, as others have correctly pointed out. Personal vehicles used for regular commuting aren't considered business assets, even if they're essential for getting to work. I'd recommend documenting your dad's financial situation as of the repossession date (assets vs. liabilities) just in case a 1099-C does arrive and you need to evaluate insolvency options.

Having dealt with a similar situation between Texas and California, I can't stress enough how important it is to establish clear, unambiguous residency rather than cutting it close. The 10-day shortage you mentioned puts you in exactly the kind of gray area that can trigger additional scrutiny. One thing I learned during my residency determination process is that consistency across all your records matters enormously. Beyond just counting days, make sure your voter registration, driver's license, bank statements, insurance policies, and even subscription services all point to your owned home as your primary address. Any inconsistencies can raise red flags. For your vacation day question - the general rule is that vacation days count toward your established "home base" at the time of travel. So if your primary residence was the rental when you took the vacation, those days would typically count toward the rental location, not the owned home. Given the potential city tax savings you're looking at, the financial stakes are probably high enough to justify making those extra trips to clearly hit the day count. The cost and stress of an audit, even if you ultimately prevail, usually far exceeds the inconvenience of a few additional trips. Better to have an iron-clad case than one that requires explaining or defending.

I went through a very similar situation last year with properties in Nevada and California. The advice everyone's given here is spot-on - being 10 days short of the threshold is exactly the kind of situation that can invite scrutiny. One thing I'd add that hasn't been mentioned much is to pay attention to your utilities usage patterns at both locations. During my residency review, they looked at electricity and gas bills to see which property showed consistent daily usage versus sporadic usage. High utility bills at your owned home during winter months (heating) or summer months (AC) can be strong evidence that it's where you actually live day-to-day. Also, if you have any recurring services like lawn care, house cleaning, or regular maintenance at your owned home, keep those records too. These show ongoing commitment to maintaining the property as your primary residence rather than just a place you occasionally visit. The fact that you already have your driver's license and voter registration at the owned home is great - that shows intent to establish residency there. Combined with making those extra trips to hit the day count clearly, you should be in a much stronger position. The peace of mind is definitely worth the inconvenience of a few additional trips.