Stupid question maybe, but does anyone know if you can deduct mileage for traveling to a gym if your doctor prescribed exercise as medical treatment? I have a written prescription for physical activity from my doctor for my back problems.

Just wanted to add another perspective on the mileage tracking issue. I was in the exact same boat last year - tons of medical appointments but zero mileage documentation. What I ended up doing was creating a simple spreadsheet with columns for Date, Destination, Purpose, and Miles. I went through my calendar, appointment confirmations, and prescription records to reconstruct all my medical trips. Then I used Google Maps to calculate the round-trip distance from my home to each location. I printed out a few sample Google Maps routes as backup documentation. The key thing I learned is to be conservative and only count direct trips. If I stopped somewhere else on the way to or from a medical appointment, I only counted the portion that was purely medical. Better to leave money on the table than risk problems later. My CPA said the documentation was more than adequate, and I ended up claiming about $340 in medical mileage deductions. Sometimes the simple approach works best!

Has anyone tried using any of the tax software packages to track S-corp basis over multiple years? I've been using a spreadsheet but it's getting unwieldy. I've heard QuickBooks doesn't really handle it well, but wondering if any of the tax packages do?

I've been dealing with S-corp basis issues for years and want to clarify something that might help. The ordering rules are actually laid out in IRC Section 1367, and they're pretty rigid: 1. Start with beginning stock basis 2. Add: Income items (including tax-exempt income) 3. Add: Additional paid-in capital contributions 4. Subtract: Distributions (but not below zero) 5. Subtract: Non-deductible expenses 6. Subtract: Losses and deductions So in your case, Henry, your $18.5k additional paid-in capital does create basis that's available for distributions before your current year loss hits. But here's the key detail some people miss - if you take a distribution that exceeds your basis after steps 1-3, that excess becomes taxable as capital gain. One more thing about those suspended losses: they stay suspended indefinitely until you create enough basis to absorb them. They don't disappear, but they also don't factor into the current year ordering calculation. Think of them as sitting in a separate bucket waiting for future basis. Documentation is crucial here. The IRS loves to challenge S-corp basis calculations on audit, so keep detailed records of when you made the capital contribution and any distributions.

Does anyone know if the tax treatment is different for RSUs vs stock options? My company gives us both and I'm completely lost about how to handle either of them on my taxes.

@Liam Sullivan - I went through this exact same confusion last year! Here's what I learned the hard way: First, your RSU income should definitely be on your W-2 in Box 1, combined with your regular salary. It won't be listed separately, which is why you might have missed it. When RSUs vest, they're treated as regular compensation income, not as a special type of income. The process is actually simpler than it seems: 1. The fair market value of your RSUs when they vested gets included in your W-2 Box 1 (wages) 2. Any taxes withheld appear in Box 2 (federal income tax withheld) 3. You report this on your 1040 just like regular wages - no special forms needed for the vesting event itself If you're absolutely certain the RSU income isn't on your W-2, that's a red flag. Your employer is required to include it. I'd recommend calling your payroll department again and specifically asking them to walk you through where the RSU income appears on your W-2. Also check if you received any supplemental documents from your company or brokerage that show the vesting details - these can help you verify the amounts even if they're combined on your W-2. The good news is once you locate it on your W-2, reporting it is straightforward since it's just regular income!

Thanks everyone for all the detailed advice! This is exactly what I needed. Just to clarify a few things based on what I'm reading: 1. My S-Corp should reimburse me for the laptop and software I paid for personally, then deduct those on the 1120-S 2. For my cell phone, I need to document the 70% business use and have the S-Corp reimburse only that portion 3. I should set up a formal accountable plan for ongoing reimbursements Quick follow-up question - if I get reimbursed by my S-Corp now (in April) for expenses I paid in January-March, does that still count for the 2024 tax year or does it become a 2025 deduction? I want to make sure I'm handling the timing correctly. Also really appreciate the warnings about reasonable salary and health insurance - I definitely need to review those areas too!

Just want to add another perspective here - I went through this exact situation with my S-Corp last year and made some mistakes that cost me. One thing I didn't see mentioned is the importance of getting your corporate bylaws and operating procedures documented properly BEFORE you start doing reimbursements. The IRS can challenge reimbursements if they don't follow proper corporate formalities. I had to go back and create board resolutions approving my expense reimbursement policy retroactively, which looked suspicious. Better to have everything documented upfront. Also, be really careful with that home office deduction. If your S-Corp is going to reimburse you for home office expenses, you need to establish a formal rental agreement between yourself and your corporation. The rent you charge should be reasonable for your area - I used comparable office space rates in my neighborhood as justification. One last tip - consider getting a separate business credit card for all S-Corp expenses going forward. It makes tracking so much easier and eliminates the need for most reimbursements. The corporation pays the bill directly and you never have to worry about the personal vs business expense classification issues.

For someone new to crypto taxes like yourself, here are the key points to remember: 1. **Yes, you need to report your crypto activity.** There's no minimum threshold - even $1 in gains needs to be reported. The IRS asks about crypto transactions right on Form 1040. 2. **What matters is your actual gains/losses, not withdrawal amounts.** If you invested $2700 and withdrew $1250, you need to calculate the difference between what you paid for the crypto you sold versus what you sold it for. 3. **For tax withholding,** I'd recommend setting aside 25-30% of any gains if you're actively trading (short-term rates). If you held for over a year, long-term capital gains rates are much lower (0%, 15%, or 20% depending on income). 4. **Start tracking everything now.** Every crypto-to-crypto trade, every sale, every purchase - it all needs to be documented. Your exchange should have transaction histories you can download. The good news is that if you had losses on some trades, those can offset your gains. But you absolutely need to report everything to stay compliant with the IRS.

One thing I'd add that hasn't been mentioned yet - make sure you understand the "wash sale" implications for crypto. While the traditional wash sale rule doesn't technically apply to crypto (since it's treated as property, not securities), the IRS has been signaling they may crack down on this. A wash sale is when you sell crypto at a loss and then buy the same or substantially identical crypto within 30 days. If you're doing this to harvest tax losses while maintaining your position, be aware this could be scrutinized. Also, don't forget about state taxes! Some states have no capital gains tax, but others will tax your crypto gains at their regular income tax rates. This can add significantly to your tax bill depending on where you live. For your $2700 investment with $1250 withdrawn, focus on calculating the actual cost basis of what you sold versus the sale price. The total amounts invested/withdrawn don't tell the whole story - it's all about the specific transactions and their timing.