I went through this exact same situation last year with a client who converted from C-corp to S-corp. The key thing that helped me was creating a detailed basis reconciliation worksheet that tracked everything chronologically. Start with the shareholder's original investment in the C-corp stock, then add any additional capital contributions made during the C-corp years, subtract any distributions received as a C-corp shareholder, and make any other basis adjustments that occurred before the S election date. That becomes your "conversion date basis." Then from the conversion date forward, you track all the normal S-corp basis adjustments (income, losses, distributions, etc.) on top of that foundation. One thing that tripped me up initially was making sure I had the exact conversion date right, because you need to split the year if they converted mid-year. The IRS is very particular about getting the timing correct for basis calculations. Also, definitely keep detailed documentation of how you calculated the beginning basis - the IRS loves to audit basis calculations on converted entities, so having a clear paper trail is essential.

This thread has been incredibly helpful! I'm dealing with my first C-corp to S-corp conversion and was completely overwhelmed by Form 7203. Reading through everyone's experiences and explanations has clarified so much. One thing I want to add that might help others - make sure you also check if there were any Section 1244 stock elections made during the C-corp years. This can affect how you treat certain losses, and I almost missed it on my client's conversion because it was buried in their old corporate records. Also, for anyone struggling with reconstructing basis when records are incomplete, don't forget to check state tax returns too. Sometimes they have additional detail that the federal returns don't show, especially regarding capital contributions or distributions that might not be obvious from just the federal filings. The advice about keeping detailed documentation cannot be overstated. I created a separate Excel workbook just for basis tracking with tabs for each year, and it's already saved me hours when the client had follow-up questions.

I'm going through the exact same situation right now! My therapist prescribed my emotional support dog for my PTSD, and I've been tracking all expenses carefully. What I've learned from researching this extensively is that the IRS hasn't changed the fundamental rules for 2024, but they are definitely scrutinizing these deductions more closely. The most important thing is having proper documentation - your doctor's letter needs to specifically state that the ESA is prescribed for treating a diagnosed mental health condition, not just general companionship. I keep a spreadsheet separating necessary medical expenses (basic food, vet visits, medications) from regular pet expenses (toys, fancy treats, decorative items). One tip that helped me: I called my doctor's office and asked them to revise my ESA letter to be more specific about the medical necessity. The original letter was too vague, but the updated version clearly connects my diagnosed condition to why I need the animal for treatment. This documentation will be crucial if you ever face questions from the IRS.

I appreciate everyone sharing their experiences! As someone who's been dealing with ESA deductions for a few years now, I wanted to add that it's also worth keeping documentation about when you acquired your emotional support animal. The IRS may want to see that the timing aligns with your diagnosed condition and treatment plan. I learned this the hard way when I had to explain why I got my ESA two years after my initial diagnosis. Fortunately, I had session notes from my therapist showing that we discussed getting an emotional support animal as part of my ongoing treatment, which helped establish the medical timeline. Also, don't forget that if you move for medical reasons related to your condition (and your ESA), some of those moving expenses might also be deductible as medical expenses. It's a lesser-known rule that could apply if you relocate to be closer to specialized care or a more suitable living environment for managing your condition.

Don't forget that if you owe more than $1,000 and didn't have proper withholding or make estimated payments throughout the year, you might face an "underpayment of estimated tax" penalty (Form 2210) regardless of when you file or pay the balance due.

This is exactly the situation I was in last year! Here's what I learned the hard way: while there's no interest benefit to paying early (since interest starts accruing after April 15th regardless), filing early gives you peace of mind and more options. What really helped me was getting on a payment plan as soon as possible. Even if you can't pay the full amount by April 15th, paying SOMETHING reduces the balance that penalties and interest accrue on. For example, if you owe $5,000 but can scrape together $2,000 by the deadline, you'll only pay penalties and interest on the remaining $3,000. Also, don't beat yourself up too much about the withholding mistakes - it happens to more people than you'd think, especially when income changes or life circumstances shift. The key is learning from it and adjusting for next year. I immediately updated my W-4 after dealing with my tax debt and started making quarterly estimated payments to avoid the same mess this year. One last tip: if you're really stressed about the numbers, consider using the IRS Online Payment Agreement tool. It shows you exactly what your monthly payments would be and the total interest/penalties you'd pay under different scenarios. Having that concrete information really helped calm my nerves.

One more angle that might help with your specific situation - since you mentioned you're having "decent luck" at both casinos and betting apps, you might want to look into whether you qualify as a "professional gambler" vs. a "recreational gambler" for tax purposes. This distinction can make a big difference in how you report your income and what expenses you can deduct. Professional gamblers can deduct gambling-related expenses (travel to casinos, gambling publications, equipment, etc.) as business expenses on Schedule C, and their gambling income isn't subject to the hobby loss limitations that recreational gamblers face. However, the IRS has strict criteria - you need to show that gambling is your primary source of income, you do it regularly and continuously, and you depend on it for your livelihood. Most casual gamblers won't qualify for professional status, but if your winnings are becoming substantial and you're spending significant time and effort on gambling activities, it might be worth researching. The professional designation also affects things like self-employment tax and retirement account contributions. Either way, definitely start keeping detailed records now before your activity gets more complex. The habits you build early will save you major headaches later!

This thread has been incredibly helpful! I'm in a similar situation as the original poster - had some good luck with sports betting apps this year and realized I have no idea what I'm doing tax-wise. One question I haven't seen addressed: what happens if you have a really good year gambling but then lose most of it back in the following tax year? Like if I win $15,000 in 2024 but then lose $12,000 of it in early 2025, I still have to pay taxes on the full $15,000 for my 2024 return, right? Those 2025 losses can't offset the 2024 winnings? Also, for anyone using the betting apps - do they automatically send you tax forms at the end of the year if you hit certain thresholds, or do you have to request your win/loss statements? I've been pretty lucky on FanDuel and DraftKings but haven't gotten any tax documents yet. Thanks to everyone who's shared their experiences here, especially about the record-keeping requirements. Definitely going to start taking screenshots of everything going forward!

Did you use one of those rewards apps or digital coupons? Sometimes the receipt shows the original price but the discount is applied after and the tax is calculated on the pre-discount amount. Makes it look like the tax percentage is higher than it actually is if you're calculating based on the final price.

I work in retail tax compliance and see this issue more often than you'd think. A 14% effective tax rate on a convenience store purchase in California is definitely wrong - even in the highest-tax jurisdictions like parts of LA County, you shouldn't see more than about 10.25% total. Here's what likely happened: Either their POS system has the wrong tax table programmed for your location, or there's a glitch where it's double-taxing certain items. Sometimes when stores update their systems or change locations within tax districts, the tax rates don't get updated properly. I'd recommend going back with your receipt and asking to speak with a manager. Most chain stores have corporate policies about fixing tax errors and will refund the difference once they verify the mistake. If they won't help, definitely file a complaint with the California Department of Tax and Fee Administration - they have an online form for reporting businesses that aren't collecting the correct tax amounts. Also keep that receipt! If this is a systematic error affecting multiple customers, you might be helping identify a bigger issue that needs to be corrected across multiple locations.